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{{Franconia}} | {{Franconia}} | ||
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<script> | <script> | ||
$(document).ready(function () { | $(document).ready(function () { | ||
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padding-right: 5%; | padding-right: 5%; | ||
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.timeline-content p{ | .timeline-content p{ | ||
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.timeline-biology .timeline-block-left .timeline-box, .timeline-chemistry .timeline-block-left .timeline-box{ | .timeline-biology .timeline-block-left .timeline-box, .timeline-chemistry .timeline-block-left .timeline-box{ | ||
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margin-left: 10%; | margin-left: 10%; | ||
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border: none; | border: none; | ||
} | } | ||
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+ | .timeline h3{ | ||
+ | padding-left: 10%; | ||
+ | } | ||
+ | |||
+ | .timeline-text{ | ||
+ | padding-left: 10%; | ||
+ | } | ||
+ | |||
+ | .marker{ | ||
+ | width: 45px; | ||
+ | height: 45px; | ||
+ | margin-left: 1%; | ||
+ | } | ||
+ | |||
+ | .marker p{ | ||
+ | font-size: 80%; | ||
+ | } | ||
.beam_image_name > h5 { | .beam_image_name > h5 { | ||
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<section id="beam2_3"> | <section id="beam2_3"> | ||
<div class="beam_image_name"> | <div class="beam_image_name"> | ||
− | <h5>Azo Dye <br>& | + | <h5>Azo Dye <br> </h5> |
</div> | </div> | ||
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</section> | </section> | ||
− | + | <section id="labjournal-chemistry"> | |
<div class="middle-banner labJournal"> | <div class="middle-banner labJournal"> | ||
<div class="banner-heading"> | <div class="banner-heading"> | ||
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</div> | </div> | ||
</div> | </div> | ||
− | <div class="content"> | + | <div class = "content"> |
− | + | <h3>Timeline</h3> | |
<div class="timeline hidden-timeline timeline-chemistry"> | <div class="timeline hidden-timeline timeline-chemistry"> | ||
− | + | <div class="timeline-block timeline-block-left"> | |
<div class="marker-right"> | <div class="marker-right"> | ||
<p>14<br>Sep</p></div> | <p>14<br>Sep</p></div> | ||
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<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | <h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> |
<p>The same reaction mixture as on 09/12/17 was purified via column chromatography | <p>The same reaction mixture as on 09/12/17 was purified via column chromatography | ||
(EtOH/DCM, 1:19) affording a yellowish-orange fraction 1, a red fraction 2 and a | (EtOH/DCM, 1:19) affording a yellowish-orange fraction 1, a red fraction 2 and a | ||
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</div> | </div> | ||
− | + | <div class="timeline-block timeline-block-right"> | |
<div class="marker-right"> | <div class="marker-right"> | ||
<p>12<br>Sep</p></div> | <p>12<br>Sep</p></div> | ||
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<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | <h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
<p>The reaction mixture from 09/07/2017, which was dissolved in Cyclohexane, turned | <p>The reaction mixture from 09/07/2017, which was dissolved in Cyclohexane, turned | ||
− | orange and a black precipitate was formed. The mixture was filtered and the | + | orange and a black precipitate was formed. The mixture was filtered and the residue |
− | + | ||
again was dissolved in 150 mL of Cyclohexane. | again was dissolved in 150 mL of Cyclohexane. | ||
The dried reaction mixture from 09/08/2017 purified via column chromatography | The dried reaction mixture from 09/08/2017 purified via column chromatography | ||
(EtOH/DCM, 1:19) affording the following fractions:</p> | (EtOH/DCM, 1:19) affording the following fractions:</p> | ||
− | + | <div class = "title"><p>Yield: </p></div> | |
− | + | <div class = table-responsive"> | |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>Description of the product</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th>Fraction 1</th> | |
− | + | <td>Orange liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 2</th> | |
− | + | <td>Reddish-orange liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 3</th> | |
− | + | <td>Red liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 4</th> | |
− | + | <td>Violet liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 5</th> | |
− | + | <td>Deep red liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 6</th> | |
− | + | <td>Violet liquid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th>Fraction 7</th> | |
− | + | <td>Violet-bluish liquid</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
− | + | </div> | |
− | + | <p>A thin-layer chromatography was performed with the fractions 1-6. Only in the TLC of | |
− | + | fraction number 3 an orange dot was visible.</p> | |
− | + | ||
</div> | </div> | ||
<button class="read-more"> | <button class="read-more"> | ||
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<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | <h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
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<tr> | <tr> | ||
<th scope="row">4-iodo-1- | <th scope="row">4-iodo-1- | ||
− | nitrosobenzene | + | nitrosobenzene</th> |
− | + | ||
<td>233,00</td> | <td>233,00</td> | ||
<td>-</td> | <td>-</td> | ||
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</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>Phenylenediamine (0,03 g; 0,28 mmol) acid in 3 mL acetic acid was added to | + | <p>Phenylenediamine (0,03 g; 0,28 mmol) acid in 3 mL acetic acid was added to 4-iodo- |
− | + | ||
1-nitrosobenzene (0,13 g; 0,56mmol). The reaction mixture was stirred at room | 1-nitrosobenzene (0,13 g; 0,56mmol). The reaction mixture was stirred at room | ||
temperature overnight. The reaction mixture was concentrated under reduced | temperature overnight. The reaction mixture was concentrated under reduced | ||
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<i class="fa fa-angle-double-down"></i> | <i class="fa fa-angle-double-down"></i> | ||
</button> | </button> | ||
+ | </div> | ||
</div> | </div> | ||
</div> | </div> | ||
</div> | </div> | ||
− | |||
<div class="timeline-block timeline-block-right"> | <div class="timeline-block timeline-block-right"> | ||
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<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | <h3>Synthesis 1,3-bis(-(4-iodophenyl)diazenyl)benzene</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
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<tr> | <tr> | ||
<th scope="row">4-iodo-1- | <th scope="row">4-iodo-1- | ||
− | nitrosobenzene | + | nitrosobenzene</th> |
− | + | ||
<td>233,00</td> | <td>233,00</td> | ||
<td>-</td> | <td>-</td> | ||
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</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>Phenylenediamine (0,05 g; 0,46 mmol) acid in 2 mL acetic acid was added to | + | <p>Phenylenediamine (0,05 g; 0,46 mmol) acid in 2 mL acetic acid was added to 4-iodo- |
− | + | ||
1-nitrosobenzene (0,215 g; 0,92mmol). The reaction mixture was stirred at room | 1-nitrosobenzene (0,215 g; 0,92mmol). The reaction mixture was stirred at room | ||
temperature over night. The reaction mixture was concentrated under reduced | temperature over night. The reaction mixture was concentrated under reduced | ||
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</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>29<br>Aug</p> | <p>29<br>Aug</p> | ||
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<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis</h3> | <h3>Synthesis</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/6/6c/T--Franconia--Beam--azide2.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/6/6c/T--Franconia--Beam--azide2.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
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<th></th> | <th></th> | ||
<th>M [g/mol]</th> | <th>M [g/mol]</th> | ||
− | + | <th>ρ [g/cm3]</th> | |
<th>V [mL]</th> | <th>V [mL]</th> | ||
<th>m [mg]</th> | <th>m [mg]</th> | ||
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<tr> | <tr> | ||
<th scope="row">Sodium | <th scope="row">Sodium | ||
− | ascorbate | + | ascorbate</th> |
− | + | ||
<td>176,13</td> | <td>176,13</td> | ||
<td>-</td> | <td>-</td> | ||
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<td>0,063</td> | <td>0,063</td> | ||
</tr> | </tr> | ||
− | + | <tr> | |
<th scope="row">Fluorenol</th> | <th scope="row">Fluorenol</th> | ||
<td>206,24</td> | <td>206,24</td> | ||
Line 1,019: | Line 1,026: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
<p>Quaterthiophene (0,745 g; 2,25 mmol) and N-bromosuccinimide (0,505 g; 2,84 mmol) | <p>Quaterthiophene (0,745 g; 2,25 mmol) and N-bromosuccinimide (0,505 g; 2,84 mmol) | ||
− | were dissolved in a mixture of CHCl 3 (2,85 mL) and cold AcOH (2,85 mL). The | + | were dissolved in a mixture of CHCl 3 (2,85 mL) and cold AcOH (2,85 mL). The reaction |
− | + | mixture then was shielded from light and stirred over night at room temperature. Following | |
− | mixture then was shielded from light and stirred over night at room temperature. | + | |
− | + | ||
the solvents were evaporated.</p> | the solvents were evaporated.</p> | ||
</div> | </div> | ||
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<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis of (Quaterthiophene-5- ylethynyl)trimethylsilane</h3> | + | <h3>Synthesis of (Quaterthiophene-5-ylethynyl)trimethylsilane</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/1/19/T--Franconia--Beam--siliane.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/1/19/T--Franconia--Beam--siliane.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,112: | Line 1,117: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p> | + | <p>The reaction mixture of α-Bromoquaterhiophene (0,4 g; 0,98 mmol), TMSA (0,167 mL), Pd(PPh3)2Cl2 (0,02 g; 0,03 mmol) and CuI (0,01 g; 0,03 mmol) in Net3 (0,4 mL) and THF (4,6 mL) was heated at 65°C over night under nitrogen atmosphere. The Solvent was removed by evaporation.</p> |
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
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− | + | ||
</div> | </div> | ||
<button class="read-more"> | <button class="read-more"> | ||
Line 1,160: | Line 1,128: | ||
</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>28<br>Aug</p> | <p>28<br>Aug</p> | ||
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<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
− | <h3>Synthesis of α- Bromquaterthiophene</h3> | + | <h3>Synthesis of α-Bromquaterthiophene</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/5/52/T--Franconia--Beam--azide1.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/5/52/T--Franconia--Beam--azide1.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,220: | Line 1,188: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
<p>Quaterthiophene (0,745 g; 2,25 mmol) and N-bromosuccinimide (0,505 g; 2,84 mmol) | <p>Quaterthiophene (0,745 g; 2,25 mmol) and N-bromosuccinimide (0,505 g; 2,84 mmol) | ||
− | were dissolved in a mixture of CHCl 3 (2,85 mL) and cold AcOH (2,85 mL). The | + | were dissolved in a mixture of CHCl 3 (2,85 mL) and cold AcOH (2,85 mL). The reaction |
− | + | mixture then was shielded from light and stirred over night at room temperature. Following | |
− | mixture then was shielded from light and stirred over night at room temperature. | + | |
− | + | ||
the solvents were evaporated.</p> | the solvents were evaporated.</p> | ||
</div> | </div> | ||
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<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis Biotin-azide ( II )</h3> | <h3>Synthesis Biotin-azide ( II )</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/e/eb/T--Franconia--Beam--ethanol.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/e/eb/T--Franconia--Beam--ethanol.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,303: | Line 1,269: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>A solution of 2-(2- (2-azidoethoxy)ethoxy)ethanol (1,08 g; 6,1 mmol) , Biotin | + | <p>A solution of 2-(2- (2-azidoethoxy)ethoxy)ethanol (1,08 g; 6,1 mmol) , Biotin (1,47 g; |
− | + | 6,0 mmol), DMAP ( 0,58 g; 4,7 mmol) and DCC (2,13 g; 11,2 mmol) in CH 2 Cl 2 (45 ml) | |
− | 6,0 mmol), DMAP ( 0,58 g; 4,7 mmol) and DCC (2,13 g; 11,2 mmol) in CH 2 Cl 2 (45 | + | |
− | + | ||
was stirred at room temperature overnight under N 2 - atmosphere. The reaction | was stirred at room temperature overnight under N 2 - atmosphere. The reaction | ||
− | mixture was filtered off and washed with a small volume of CH 2 Cl 2. Following | + | mixture was filtered off and washed with a small volume of CH 2 Cl 2. Following the |
− | + | crude product was purified by silica gel chromatography column (CH 2 Cl 2 / MeOH, | |
− | crude product was purified by silica gel chromatography column (CH 2 Cl 2 / | + | |
− | + | ||
30:1) and the solvent was removed in a rotary evaporator.</p> | 30:1) and the solvent was removed in a rotary evaporator.</p> | ||
</div> | </div> | ||
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</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>24<br>Aug</p> | <p>24<br>Aug</p> | ||
Line 1,331: | Line 1,293: | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis Biotin-azide ( I )</h3> | <h3>Synthesis Biotin-azide ( I )</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/ | + | <img src = "https://static.igem.org/mediawiki/2017/e/eb/T--Franconia--Beam--ethanol.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,341: | Line 1,303: | ||
<th></th> | <th></th> | ||
<th>M [g/mol]</th> | <th>M [g/mol]</th> | ||
− | + | <th>ρ [g/cm3]</th> | |
<th>V [mL]</th> | <th>V [mL]</th> | ||
<th>m [mg]</th> | <th>m [mg]</th> | ||
Line 1,392: | Line 1,354: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>A solution of 2-(2- (2-azidoethoxy)ethoxy)ethanol (1,02 g; 5,8 mmol) , Biotin | + | <p>A solution of 2-(2- (2-azidoethoxy)ethoxy)ethanol (1,02 g; 5,8 mmol) , Biotin (1,49 g; |
− | + | 6,1 mmol), DMAP ( 0,57 g; 4,6 mmol) and DCC (2,11 g; 10,2 mmol) in CH 2 Cl 2 (45 ml) | |
− | 6,1 mmol), DMAP ( 0,57 g; 4,6 mmol) and DCC (2,11 g; 10,2 mmol) in CH 2 Cl 2 (45 | + | |
− | + | ||
was stirred at room temperature overnight under N 2 - atmosphere. The reaction | was stirred at room temperature overnight under N 2 - atmosphere. The reaction | ||
− | mixture was filtered off and washed with a small volume of CH 2 Cl 2. Following | + | mixture was filtered off and washed with a small volume of CH 2 Cl 2. Following the |
− | + | crude product was purified by silica gel chromatography column (CH 2 Cl 2 / MeOH, | |
− | crude product was purified by silica gel chromatography column (CH 2 Cl 2 / | + | |
− | + | ||
30:1) and the solvent was removed in a rotary evaporator.</p> | 30:1) and the solvent was removed in a rotary evaporator.</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,449: | Line 1,407: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 2-(2- (2-azidoethoxy)ethoxy)ethanol</h3> | + | <h3>Synthesis 2-(2-(2-azidoethoxy)ethoxy)ethanol</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/b/bf/T--Franconia--Beam--2222.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/b/bf/T--Franconia--Beam--2222.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,469: | Line 1,427: | ||
<tr> | <tr> | ||
<th scope="row">2-(2-(2-chloroethoxy)ethoxy)ethano | <th scope="row">2-(2-(2-chloroethoxy)ethoxy)ethano | ||
− | l | + | l</th> |
− | + | ||
<td>168,62</td> | <td>168,62</td> | ||
<td>1,16</td> | <td>1,16</td> | ||
Line 1,506: | Line 1,463: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>At first 2-(2- (2-chloroethoxy)ethoxy)ethanol (2,51 g; 14,9 mmol) and NaN 3 (1,00 | + | <p>At first 2-(2- (2-chloroethoxy)ethoxy)ethanol (2,51 g; 14,9 mmol) and NaN 3 (1,00 g; |
− | + | ||
15,4 mmol) were reacted in DMF (25 mL) overnight at 100°C. The mixture following | 15,4 mmol) were reacted in DMF (25 mL) overnight at 100°C. The mixture following | ||
cooling down was diluted with THF (25 mL) and filtered. After the solvent was | cooling down was diluted with THF (25 mL) and filtered. After the solvent was | ||
− | removed, the residue was dissolved in diethyl ether (100 mL), washed with brine | + | removed, the residue was dissolved in diethyl ether (100 mL), washed with brine (20 |
− | + | mL) and dried over MgSO 4 . 2-(2- (2-azidoethoxy)ethoxy)ethanol was isolated as a | |
− | mL) and dried over MgSO 4 . 2-(2- (2-azidoethoxy)ethoxy)ethanol was isolated as | + | |
− | + | ||
yellowish orange solid.</p> | yellowish orange solid.</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,537: | Line 1,491: | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Yellowish orange solid</td> | + | <td colspan = 3>Yellowish orange solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
Line 1,551: | Line 1,505: | ||
</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>22<br>Aug</p> | <p>22<br>Aug</p> | ||
Line 1,558: | Line 1,512: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,578: | Line 1,532: | ||
<tr> | <tr> | ||
<th scope="row">4-iodo-1- | <th scope="row">4-iodo-1- | ||
− | nitrobenzene | + | nitrobenzene</th> |
− | + | ||
<td>249,01</td> | <td>249,01</td> | ||
<td>-</td> | <td>-</td> | ||
Line 1,603: | Line 1,556: | ||
<td>0,7</td> | <td>0,7</td> | ||
<td>13,09</td> | <td>13,09</td> | ||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
</tr> | </tr> | ||
<tr> | <tr> | ||
Line 1,639: | Line 1,584: | ||
</table> | </table> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo-1-nitrobenzen (2,00 g; 8,03 mmol) was dissolved in 60 mL 2-methoxyethanol. | + | <p>4-Iodo-1-nitrobenzen (2,00 g; 8,03 mmol) was dissolved in 60 mL 2-methoxyethanol. Zn |
− | + | dust (1,39 g; 21,26 mmol) and NH4Cl (0,7 g; 13,09 mmol) was added and the reaction | |
− | dust (1,39 g; 21,26 mmol) and NH4Cl (0,7 g; 13,09 mmol) was added and the | + | |
− | + | ||
mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | ||
− | hexanes/EtOAc). After 45 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O | + | hexanes/EtOAc). After 45 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O (6,55 g; |
− | + | 24,23 mmol) was solved in 72 mL H2O/EtOH (5:1) and added to the reaction mixture which | |
− | 24,23 mmol) was solved in 72 mL H2O/EtOH (5:1) and added to the reaction mixture | + | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted with EtOAc (3 |
− | + | ||
− | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted | + | |
− | + | ||
× 80 mL), washed with brine and dried over MgSO4. The received solution was | × 80 mL), washed with brine and dried over MgSO4. The received solution was | ||
− | concentrated under reduced pressure and purified by silica gel column | + | concentrated under reduced pressure and purified by silica gel column chromatography |
− | + | (hexanes/EtOAc, 50:1). The solvent was removed and the product 4-iodo-1-nitrosobenzen | |
− | (hexanes/EtOAc, 50:1). The solvent was removed and the product | + | |
− | + | ||
(0,472 g; 2,03 mmol) was received as a green solid.</p> | (0,472 g; 2,03 mmol) was received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,671: | Line 1,609: | ||
<tr> | <tr> | ||
<th>4-iodo-1-nitrosobenzen | <th>4-iodo-1-nitrosobenzen | ||
− | (fraction 5 and 6) | + | (fraction 5 and 6)</th> |
− | + | ||
<td>233,0</td> | <td>233,0</td> | ||
<td>0,472</td> | <td>0,472</td> | ||
Line 1,680: | Line 1,617: | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan="3">Green solid</td> | + | <td colspan = "3">Green solid</td> |
</tr> | </tr> | ||
Line 1,700: | Line 1,637: | ||
<div class="timeline-content"> | <div class="timeline-content"> | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
− | div class="timeline-text biggerPicture"> | + | <div class="timeline-text biggerPicture"> |
− | + | <h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | |
− | + | <div class = "title"><p>Chemical equation:</p></div> | |
− | + | <img src = "https://static.igem.org/mediawiki/2017/b/bb/T--Franconia--Beam--bromquater.png"> | |
+ | <div class="read-more-content"> | ||
+ | <div class = "title"><p>Reagents:</p></div> | ||
+ | <div class = table-responsive"> | ||
+ | <table class="table"> | ||
+ | <thead> | ||
+ | <tr> | ||
+ | <th></th> | ||
+ | <th>M [g/mol]</th> | ||
+ | <th>ρ [g/cm<sup>3</sup>]</th> | ||
+ | <th>V [mL]</th> | ||
+ | <th>m [g]</th> | ||
+ | <th>n [mmol]</th> | ||
+ | </tr> | ||
+ | </thead> | ||
+ | <tbody> | ||
+ | <tr> | ||
+ | <th scope="row">4-iodo-1-nitrosobenzene</th> | ||
+ | <td>233,00</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | <td>0,055</td> | ||
+ | <td>0,24</td> | ||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Acetic acid</th> | ||
+ | <td>152,20</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | <td>0,017</td> | ||
+ | <td>0,11</td> | ||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Acetic acid</th> | ||
+ | <td>60,05</td> | ||
+ | <td>1,05</td> | ||
+ | <td>2</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | </tr> | ||
+ | </tbody> | ||
+ | </table> | ||
+ | </div> | ||
+ | <div class = "title"><p>Procedure:</p></div> | ||
+ | <p>3,5-diaminobenzoic (0,017 g; 0,11 mmol) acid in 2 mL acetic acid was added to 4- | ||
+ | iodo-1- nitrosobenzene (0,055 g; 0,24 mmol). The reaction mixture was stirred at | ||
+ | room temperature for four days. The reaction mixture was concentrated under | ||
+ | reduced pressure and purified via column chromatography (EtOH/DCM, 1:19). | ||
+ | </p> | ||
+ | </div> | ||
+ | <button class="read-more"> | ||
+ | <i class="fa fa-angle-double-down"></i> | ||
+ | </button> | ||
+ | </div> | ||
+ | </div> | ||
+ | </div> | ||
+ | </div> | ||
+ | |||
+ | <div class="timeline-block timeline-block-right"> | ||
+ | <div class="marker-right"> | ||
+ | <p>16<br>Jun</p></div> | ||
+ | <div class="timeline-content"> | ||
+ | <div class="timeline-box"> | ||
+ | <div class="timeline-text biggerPicture"> | ||
+ | <h3>Synthesis 3,5-bis(4-(trimethylsilyl)phenyl)diazenyl)benzoic acid</h3> | ||
+ | <div class = "title"><p>Chemical equation:</p></div> | ||
+ | <img src = "https://static.igem.org/mediawiki/2017/0/05/T--Franconia--Beam--Sisisi.png"> | ||
+ | <div class="read-more-content"> | ||
+ | <div class = "title"><p>Reagents:</p></div> | ||
+ | <div class = table-responsive"> | ||
+ | <table class="table"> | ||
+ | <thead> | ||
+ | <tr> | ||
+ | <th></th> | ||
+ | <th>M [g/mol]</th> | ||
+ | <th>ρ [g/cm<sup>3</sup>]</th> | ||
+ | <th>V [mL]</th> | ||
+ | <th>m [g]</th> | ||
+ | <th>n [mmol]</th> | ||
+ | </tr> | ||
+ | </thead> | ||
+ | <tbody> | ||
+ | <tr> | ||
+ | <th scope="row">4-iodo-1-nitrosobenzene</th> | ||
+ | <td>233,00</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | <td>0,125</td> | ||
+ | <td>0,53</td> | ||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Acetic acid</th> | ||
+ | <td>152,20</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | <td>0,048</td> | ||
+ | <td>0,32</td> | ||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Acetic acid</th> | ||
+ | <td>60,05</td> | ||
+ | <td>1,05</td> | ||
+ | <td>4</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | </tr> | ||
+ | </tbody> | ||
+ | </table> | ||
+ | </div> | ||
+ | <p>(Fraction 3 and 4 of trimethyl((4-nitrosophenyl)ethynyl)silane from May 31th were | ||
+ | added together)</p> | ||
+ | <div class = "title"><p>Procedure:</p></div> | ||
+ | <p>3,5-diaminobenzoic (0,048 g; 0,32 mmol) acid in 4 mL acetic acid was added to trimethyl((4-nitrosophenyl)ethynyl)silane (0,125 g; 0,53 mmol). The reaction mixture was stirred at room temperature for four days. The reaction mixture was concentrated under reduced pressure and purified via column chromatography (EtOH/DCM, 1:19). | ||
+ | </p> | ||
+ | </div> | ||
+ | <button class="read-more"> | ||
+ | <i class="fa fa-angle-double-down"></i> | ||
+ | </button> | ||
+ | </div> | ||
+ | </div> | ||
+ | </div> | ||
+ | </div> | ||
+ | |||
+ | <div class="timeline-block timeline-block-left" > | ||
+ | <div class="marker-left"> | ||
+ | <p>08<br>Jun</p> | ||
+ | </div> | ||
+ | <div class="timeline-content"> | ||
+ | <div class="timeline-box"> | ||
+ | <div class="timeline-text"> | ||
+ | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> | ||
+ | <div class = "title"><p>Chemical equation:</p></div> | ||
+ | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | ||
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 1,721: | Line 1,794: | ||
<tr> | <tr> | ||
<th scope="row">4-iodo-1-nitrosobenzene</th> | <th scope="row">4-iodo-1-nitrosobenzene</th> | ||
− | <td> | + | <td>249,01</td> |
<td>-</td> | <td>-</td> | ||
<td>-</td> | <td>-</td> | ||
− | <td> | + | <td>4,03</td> |
− | <td> | + | <td>16,2</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
− | <th scope="row"> | + | <th scope="row">Zn</th> |
− | <td> | + | <td>65,38</td> |
<td>-</td> | <td>-</td> | ||
<td>-</td> | <td>-</td> | ||
− | <td> | + | <td>2,37</td> |
− | <td> | + | <td>36,2</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
− | <th scope="row"> | + | <th scope="row">NH<sub>4</sub>Cl</th> |
− | <td> | + | <td>53,49</td> |
− | <td>1, | + | <td>-</td> |
− | <td>2</td> | + | <td>-</td> |
+ | <td>1,42</td> | ||
+ | <td>26,5</td> | ||
+ | </tr> | ||
+ | <tr> | ||
+ | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | ||
+ | <td>270,29</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | <td>13,09</td> | ||
+ | <td>48,4</td> | ||
+ | </tr> | ||
+ | <tr> | ||
+ | <th scope="row">2-methoxyethanol</th> | ||
+ | <td>76,09</td> | ||
+ | <td>0,97</td> | ||
+ | <td>130</td> | ||
+ | <td>-</td> | ||
+ | <td>-</td> | ||
+ | </tr> | ||
+ | <tr> | ||
+ | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | ||
+ | <td>18,00/46,07</td> | ||
+ | <td>1,00/0,79</td> | ||
+ | <td>144</td> | ||
<td>-</td> | <td>-</td> | ||
<td>-</td> | <td>-</td> | ||
Line 1,748: | Line 1,845: | ||
</table> | </table> | ||
</div> | </div> | ||
− | + | <div class = "title"><p>Procedure:</p></div> | |
− | + | <p>4-Iodo-1-nitrobenzen (4,05 g; 16,3 mmol) was dissolved in 130 mL 2-methoxyethanol. Zn | |
− | <div class="title"><p>Procedure:</p></div> | + | dust (2,37 g; 36,2 mmol) and NH4Cl (1,41 g; 26,4 mmol) was added and the reaction |
− | <p> | + | mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 |
− | + | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O (13,00 g; | |
− | + | 48,1 mmol) was solved in 144 mL H2O/EtOH (5:1) and added to the reaction mixture which | |
− | reduced pressure and purified | + | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted with EtOAc, |
− | </p> | + | washed with brine and dried over MgSO4. The yielded solution was concentrated under |
+ | reduced pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). | ||
+ | The solvent was removed and the product 4-iodo-1-nitrosobenzen (0,76 g; 3,3 mmol; 20%) | ||
+ | was received as a green solid.</p> | ||
+ | <div class = "title"><p>Yield: </p></div> | ||
+ | <div class = table-responsive"> | ||
+ | <table class="table"> | ||
+ | <thead> | ||
+ | <tr> | ||
+ | <th>Product</th> | ||
+ | <th colspan = "4">4-iodo-1-nitrosobenzen</th> | ||
+ | </tr> | ||
+ | </thead> | ||
+ | <tbody> | ||
+ | <tr> | ||
+ | <th scope="row"></th> | ||
+ | <th>M [g/mol]</th> | ||
+ | <th>m[mg]</th> | ||
+ | <th>n[mmol]</th> | ||
+ | <td>Description of Product</td> | ||
+ | |||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Fraction 1</th> | ||
+ | <td>233,0</td> | ||
+ | <td>1,147</td> | ||
+ | <td>5,0</td> | ||
+ | <td>Green Solid</td> | ||
+ | </tr> | ||
+ | |||
+ | <tr> | ||
+ | <th scope="row">Fraction 1</th> | ||
+ | <td>233,0</td> | ||
+ | <td>0,098</td> | ||
+ | <td>0,4</td> | ||
+ | <td>Green Solid</td> | ||
+ | </tr> | ||
+ | </tbody> | ||
+ | </table> | ||
+ | </div> | ||
</div> | </div> | ||
<button class="read-more"> | <button class="read-more"> | ||
Line 1,762: | Line 1,899: | ||
</div> | </div> | ||
</div> | </div> | ||
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− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
− | |||
</div> | </div> | ||
− | + | </div> | |
− | + | <div id = "top-post" class="timeline-block timeline-block-right"> | |
− | <div id="top-post" class="timeline-block timeline-block-right"> | + | |
<div class="marker-right"> | <div class="marker-right"> | ||
<p>31<br>May</p></div> | <p>31<br>May</p></div> | ||
Line 1,906: | Line 1,908: | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
<h3>Synthesis trimethyl((4-nitrosophenyl)ethynyl)silane</h3> | <h3>Synthesis trimethyl((4-nitrosophenyl)ethynyl)silane</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/7/7b/T--Franconia--Beam--silane.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/7/7b/T--Franconia--Beam--silane.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M[g/mol]</th> | |
− | + | <th>V[mL]</th> | |
− | + | <th>m[mg]</th> | |
− | + | <th>n[mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">Cul</th> | |
− | + | <td>190,45</td> | |
− | + | <td>-</td> | |
− | + | <td>0,057</td> | |
− | + | <td>0,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub></th> | |
− | + | <td>701,90</td> | |
− | + | <td>-</td> | |
− | + | <td>0,105</td> | |
− | + | <td>0,2</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">TMS</th> | |
− | + | <td>98,22</td> | |
− | + | <td>0,55</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">TEA</th> | |
− | + | <td>101,19</td> | |
− | + | <td>0,55</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-<br>nitrosobenzen</th> | |
− | + | <td>232,92</td> | |
− | + | <td>-</td> | |
− | + | <td>1,17</td> | |
− | + | <td>5,0</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">THF</th> | |
− | + | <td>72,11</td> | |
− | + | <td>10,0</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
<div class="table-responsive"> | <div class="table-responsive"> | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-iodo-1-nitrosobenzen (1,17 g, 5,0 mmol), CuI (0,057 g, 0,3 mmol) and | + | <p>4-iodo-1-nitrosobenzen (1,17 g, 5,0 mmol), CuI (0,057 g, 0,3 mmol) and Pd(PPh3)2Cl2 (0,105 g, 0,2 mmol) in TMS (0,55 mL), TEA (0,55 mL) and THF (10,0 mL) were stirred at 55°C under nitrogen overnight. The reaction mixture was washed with brine, concentrated under reduced pressure and purified by silica gel column chromatography (hexanes/EtOAc, 35:1).</p> |
− | + | <div class = "title"><p>Yield: </p></div> | |
− | + | <div class = table-responsive"> | |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th>Product</th> | |
− | + | <th colspan = 4>trimethyl((4-nitrosophenyl)ethynyl)silane</th> | |
− | <div class="title"><p>Yield: </p></div> | + | </tr> |
− | <div class=table-responsive"> | + | </thead> |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>m[mg]</th> | |
− | + | <th>n[mmol]</th> | |
− | + | <th>Description of | |
− | + | product</th> | |
− | + | </tr> | |
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | <tr> | |
− | + | <th scope="row">Fraction 2</th> | |
− | + | <td>203,32</td> | |
− | + | <td>0,090</td> | |
− | + | <td>0,44</td> | |
− | + | <td>Orange solid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Fraction 3</th> | |
− | + | <td>203,32</td> | |
− | + | <td>0,094</td> | |
− | + | <td>0,46</td> | |
− | + | <td>Yellow solid</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Fraction 4</th> | |
− | + | <td>203,32</td> | |
− | + | <td>0,031</td> | |
− | + | <td>0,15</td> | |
− | + | <td>Brown solid</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
</div> | </div> | ||
Line 2,034: | Line 2,028: | ||
</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>23<br>May</p> | <p>23<br>May</p> | ||
Line 2,042: | Line 2,036: | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis 3,5-bis((4-((trimethylsilyl)ethynyl)phenyl)<br>diazenyl)benzoic acid</h3> | <h3>Synthesis 3,5-bis((4-((trimethylsilyl)ethynyl)phenyl)<br>diazenyl)benzoic acid</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/c/c0/T--Franconia--Beam--lang.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/c/c0/T--Franconia--Beam--lang.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [mg]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">Cul</th> | |
− | + | <td>190,45</td> | |
− | + | <td>-</td> | |
− | + | <td>14,80</td> | |
− | + | <td>0,072</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Pd(PPh<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub></th> | |
− | + | <td>701,90</td> | |
− | + | <td>-</td> | |
− | + | <td>25,59</td> | |
− | + | <td>0,036</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">TMS</th> | |
− | + | <td>98,22</td> | |
− | + | <td>0,2</td> | |
− | + | <td>-</td> | |
− | + | <td>1,44</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">TEA</th> | |
− | + | <td>101,19</td> | |
− | + | <td>0,2</td> | |
− | + | <td>-</td> | |
− | + | <td>1,44</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">3,5-bis((4- | |
− | + | iodophenyl)diazenyl)-benzoic acid</th> | |
− | + | <td>328,19</td> | |
− | + | <td>-</td> | |
− | + | <td>251,51</td> | |
− | + | <td>1,2</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">THF</th> | |
− | + | <td>72,11</td> | |
− | + | <td>5,0</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
− | + | ||
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>3,5-bis((4-iodophenyl)diazenyl)-benzoic acid (251,51 mg, 1,2 mmol), CuI (14,80 | + | <p>3,5-bis((4-iodophenyl)diazenyl)-benzoic acid (251,51 mg, 1,2 mmol), CuI (14,80 mg, 0,072 |
− | + | mmol) and Pd(PPh3)2Cl2 (25,59 mg, 0,036 mmol) in TMS (0,2 mL), TEA (0,2 mL) and THF | |
− | + | ||
− | mmol) and Pd(PPh3)2Cl2 (25,59 mg, 0,036 mmol) in TMS (0,2 mL), TEA (0,2 mL) and | + | |
− | + | ||
(5,0 mL) were stirred at 55°C under nitrogen overnight. The reaction mixture was | (5,0 mL) were stirred at 55°C under nitrogen overnight. The reaction mixture was | ||
− | concentrated under reduced pressure and purified by silica gel column | + | concentrated under reduced pressure and purified by silica gel column chromatography |
− | + | ||
(EtOH/DCM, 1:19).</p> | (EtOH/DCM, 1:19).</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 2,132: | Line 2,121: | ||
<th>3,5-bis((4-((trimethylsilyl)-<br> | <th>3,5-bis((4-((trimethylsilyl)-<br> | ||
ethynyl)phenyl)diazenyl)-y<br> | ethynyl)phenyl)diazenyl)-y<br> | ||
− | benzoic acid | + | benzoic acid</th> |
− | + | ||
<td>522,76</td> | <td>522,76</td> | ||
<td>0,218</td> | <td>0,218</td> | ||
Line 2,141: | Line 2,129: | ||
<tr> | <tr> | ||
<th scope="row">Yield</th> | <th scope="row">Yield</th> | ||
− | <td colspan="3">Practically: 33%</td> | + | <td colspan = "3">Practically: 33%</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan="3">Orange solid</td> | + | <td colspan = "3">Orange solid</td> |
</tr> | </tr> | ||
Line 2,168: | Line 2,156: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>249,01</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>4,05</td> | |
− | + | <td>16,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Zn</th> | |
− | + | <td>65,38</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>2,37</td> | |
− | + | <td>36,2</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">NH<sub>4</sub>Cl</th> | |
− | + | <td>53,49</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,41</td> | |
− | + | <td>26,4</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | |
− | + | <td>270,29</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>13,00</td> | |
− | + | <td>48,1</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">2-methoxyethanol</th> | |
− | + | <td>76,09</td> | |
− | + | <td>0,97</td> | |
− | + | <td>130</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | |
− | + | <td>18,00/46,07</td> | |
− | + | <td>1,00/0,79</td> | |
− | + | <td>144</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo-1-nitrobenzen (4,05 g; 16,3 mmol) was dissolved in 130 mL | + | <p>4-Iodo-1-nitrobenzen (4,05 g; 16,3 mmol) was dissolved in 130 mL 2-methoxyethanol. Zn |
− | + | dust (2,37 g; 36,2 mmol) and NH4Cl (1,41 g; 26,4 mmol) was added and the reaction | |
− | dust (2,37 g; 36,2 mmol) and NH4Cl (1,41 g; 26,4 mmol) was added and the | + | |
− | + | ||
mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | ||
− | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O | + | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O (13,00 g; |
− | + | 48,1 mmol) was solved in 144 mL H2O/EtOH (5:1) and added to the reaction mixture which | |
− | 48,1 mmol) was solved in 144 mL H2O/EtOH (5:1) and added to the reaction mixture | + | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted with EtOAc, |
− | + | washed with brine and dried over MgSO4. The yielded solution was concentrated under | |
− | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted | + | reduced pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). |
− | + | The solvent was removed and the product 4-iodo-1-nitrosobenzen (0,76 g; 3,3 mmol; 20%) | |
− | + | ||
− | washed with brine and dried over MgSO4. The yielded solution was concentrated | + | |
− | + | ||
− | reduced pressure and purified by silica gel column chromatography | + | |
− | + | ||
− | + | ||
− | The solvent was removed and the product 4-iodo-1-nitrosobenzen (0,76 g; 3,3 | + | |
− | + | ||
− | + | ||
was received as a green solid.</p> | was received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 2,282: | Line 2,259: | ||
<tr> | <tr> | ||
<th scope="row">Yield</th> | <th scope="row">Yield</th> | ||
− | <td colspan=1.5>Literature: 82%</td> | + | <td colspan = 1.5>Literature: 82%</td> |
− | <td colspan=1.5>Practically: 20%</td> | + | <td colspan = 1.5>Practically: 20%</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Green solid</td> | + | <td colspan = 3>Green solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
Line 2,302: | Line 2,279: | ||
</div> | </div> | ||
− | <div class="timeline-block timeline-block-left"> | + | <div class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>06<br>Apr</p> | <p>06<br>Apr</p> | ||
Line 2,309: | Line 2,286: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>249,01</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>3,991</td> | |
− | + | <td>16,03</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Zn</th> | |
− | + | <td>65,38</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>2,388</td> | |
− | + | <td>36,52</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">NH<sub>4</sub>Cl</th> | |
− | + | <td>53,49</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,386</td> | |
− | + | <td>25,91</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | |
− | + | <td>270,29</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>13,108</td> | |
− | + | <td>48,49</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">2-methoxyethanol</th> | |
− | + | <td>76,09</td> | |
− | + | <td>0,97</td> | |
− | + | <td>120</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | |
− | + | <td>18,00/46,07</td> | |
− | + | <td>1,00/0,79</td> | |
− | + | <td>144</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo-1-nitrobenzen (3,991 g; 16,03 mmol) was dissolved in 120 mL | + | <p>4-Iodo-1-nitrobenzen (3,991 g; 16,03 mmol) was dissolved in 120 mL 2-methoxyethanol. Zn |
− | + | dust (2,388 g; 36,52 mmol) and NH4Cl (1,386 g; 25,91 mmol) was added and the reaction | |
− | + | ||
− | dust (2,388 g; 36,52 mmol) and NH4Cl (1,386 g; 25,91 mmol) was added and the | + | |
− | + | ||
mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | ||
− | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O | + | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O (13,108 g; |
− | + | 48,49 mmol) was solved in 144 mL H2O/EtOH (5:1) and added to the reaction mixture which | |
− | 48,49 mmol) was solved in 144 mL H2O/EtOH (5:1) and added to the reaction | + | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted with EtOAc, |
− | + | washed with brine and dried over MgSO4. The yielded solution was concentrated under | |
− | + | reduced pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). | |
− | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted | + | The solvent was removed and the product 4-iodo-1-nitrosobenzen (0,541 g; 2,3 mmol; |
− | + | ||
− | + | ||
− | washed with brine and dried over MgSO4. The yielded solution was concentrated | + | |
− | + | ||
− | reduced pressure and purified by silica gel column chromatography | + | |
− | + | ||
− | + | ||
− | The solvent was removed and the product 4-iodo-1-nitrosobenzen (0,541 g; 2,3 | + | |
− | + | ||
14%) was received as a green solid.</p> | 14%) was received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p> | + | <div class = "title"><p>Yield: </p> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 2,424: | Line 2,389: | ||
<tr> | <tr> | ||
<th scope="row">Yield</th> | <th scope="row">Yield</th> | ||
− | <td colspan=1.5>Literature: 82%</td> | + | <td colspan = 1.5>Literature: 82%</td> |
− | <td colspan=1.5>Practically: 14%</td> | + | <td colspan = 1.5>Practically: 14%</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Green solid</td> | + | <td colspan = 3>Green solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
Line 2,444: | Line 2,409: | ||
</div> | </div> | ||
</div> | </div> | ||
− | |||
<div class="timeline-block timeline-block-right"> | <div class="timeline-block timeline-block-right"> | ||
<div class="marker-right"> | <div class="marker-right"> | ||
Line 2,452: | Line 2,416: | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | <h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>233,00</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,2</td> | |
− | + | <td>5,15</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>152,20</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,32</td> | |
− | + | <td>2,6</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>60,05</td> | |
− | + | <td>1,05</td> | |
− | + | <td>30</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>3,5-diaminobenzoic acid (0,32 g; 2,60 mmol) and 30 mL acetic acid was added to | + | <p>3,5-diaminobenzoic acid (0,32 g; 2,60 mmol) and 30 mL acetic acid was added to 4-iodo-1- |
− | + | nitrosobenzene (1,2 g; 5,15 mmol). The reaction mixture was stirred at room temperature | |
− | nitrosobenzene (1,2 g; 5,15 mmol). The reaction mixture was stirred at room | + | overnight. The reaction mixture was concentrated under reduced pressure and purified via |
− | + | ||
− | overnight. The reaction mixture was concentrated under reduced pressure and | + | |
− | + | ||
− | + | ||
column chromatography (EtOH/DCM, 1:19).</p> | column chromatography (EtOH/DCM, 1:19).</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 2,522: | Line 2,482: | ||
<tr> | <tr> | ||
<th scope="row">3,5-bis((4-iodophenyl)<br> | <th scope="row">3,5-bis((4-iodophenyl)<br> | ||
− | diazenyl)benzoic<br> acid | + | diazenyl)benzoic<br> acid</th> |
− | + | <td colspan = 1.5>328,19</td> | |
− | <td colspan=1.5>328,19</td> | + | <td colspan = 1.5>0,509</td> |
− | <td colspan=1.5>0,509</td> | + | <td colspan = 1.5>1,6</td> |
− | <td colspan=1.5>1,6</td> | + | |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Orange/brown solid</td> | + | <td colspan = 3>Orange/brown solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
Line 2,545: | Line 2,504: | ||
</div> | </div> | ||
− | <div style="margin-top: 27%" class="timeline-block timeline-block-left"> | + | <div style = "margin-top: 27%"class="timeline-block timeline-block-left" > |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>05<br>Apr</p> | <p>05<br>Apr</p> | ||
Line 2,552: | Line 2,511: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>249,01</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>4,06</td> | |
− | + | <td>16,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Zn</th> | |
− | + | <td>65,38</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>2,53</td> | |
− | + | <td>35,7</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">NH<sub>4</sub>Cl</th> | |
− | + | <td>53,49</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,43</td> | |
− | + | <td>26,7</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | |
− | + | <td>270,29</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>12,98</td> | |
− | + | <td>48,0</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">2-methoxyethanol</th> | |
− | + | <td>76,09</td> | |
− | + | <td>0,97</td> | |
− | + | <td>200</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | |
− | + | <td>18,00/46,07</td> | |
− | + | <td>1,00/0,79</td> | |
− | + | <td>144</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo-1-nitrobenzene (4,06 g; 16,3 mmol) was dissolved in 200 mL | + | <p>4-Iodo-1-nitrobenzene (4,06 g; 16,3 mmol) was dissolved in 200 mL 2-methoxyethanol. Zn |
− | + | dust (2,53 g; 35,7 mmol) and NH4Cl (1,43 g; 26,7 mmol) was added and the reaction | |
− | + | ||
− | dust (2,53 g; 35,7 mmol) and NH4Cl (1,43 g; 26,7 mmol) was added and the | + | |
− | + | ||
mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | mixture was stirred at room temperature. The reaction was monitored by TLC (5:1 | ||
− | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O | + | hexanes/EtOAc). After 30 minutes the solution was cooled to 0°C. FeCl3 × 6 H2O (12,98 g; |
− | + | 48,0 mmol) was solved in 72 mL H2O/EtOH (5:1) and added to the reaction mixture which | |
− | 48,0 mmol) was solved in 72 mL H2O/EtOH (5:1) and added to the reaction mixture | + | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted with EtOAc, |
− | + | washed with brine and dried over MgSO4. The yielded solution was concentrated under | |
− | then was stirred 3 hours at 0°C. Following the reaction mixture was extracted | + | reduced pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). |
− | + | The solvent was removed and the product 4-iodo-1-nitrosobenzene (1,2 g; 5,2 mmol; 32%) | |
− | + | ||
− | washed with brine and dried over MgSO4. The yielded solution was concentrated | + | |
− | + | ||
− | reduced pressure and purified by silica gel column chromatography | + | |
− | + | ||
− | + | ||
− | The solvent was removed and the product 4-iodo-1-nitrosobenzene (1,2 g; 5,2 | + | |
− | + | ||
− | + | ||
was received as a green solid.</p> | was received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p> | + | <div class = "title"><p>Yield: </p> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
Line 2,667: | Line 2,614: | ||
<tr> | <tr> | ||
<th scope="row">Yield</th> | <th scope="row">Yield</th> | ||
− | <td colspan=1.5>Literature: 82%</td> | + | <td colspan = 1.5>Literature: 82%</td> |
− | <td colspan=1.5>Practically: 32%</td> | + | <td colspan = 1.5>Practically: 32%</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Green solid</td> | + | <td colspan = 3>Green solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
Line 2,687: | Line 2,634: | ||
</div> | </div> | ||
</div> | </div> | ||
− | |||
<div class="timeline-block timeline-block-right"> | <div class="timeline-block timeline-block-right"> | ||
<div class="marker-right"> | <div class="marker-right"> | ||
Line 2,695: | Line 2,641: | ||
<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | <h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <div class = "title"><p>Reagents:</p></div> | |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>233,00</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,863</td> | |
− | + | <td>3,7</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>152,20</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,299</td> | |
− | + | <td>2,0</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>60,05</td> | |
− | + | <td>1,05</td> | |
− | + | <td>25</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | + | <div class = "title"><p>Procedure:</p></div> | |
− | + | <p>3,5-diaminobenzoic (0,299 g; 2,0 mmol) acid in 25 mL acetic acid was added to 4-iodo-1- | |
− | + | nitrosobenzene (0,863 g; 3,7 mmol). The reaction mixture was stirred at room temperature | |
− | + | for four days. The reaction mixture was concentrated under reduced pressure and purified | |
− | + | via column chromatography (EtOH/DCM, 1:19). | |
− | + | <br>Fraction 3 was solved in 10 mL THF/water (1:1). | |
− | + | <br>Fraction 4 was solved in 5 mL THF/water (1:1). | |
− | + | </p> | |
− | + | <div class = "title"><p>Yield: </p></div> | |
− | + | <div class = table-responsive"> | |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th>Product</th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>m[mg]</th> | |
− | + | <th>n[mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">3,5-bis((4-iodophenyl)<br> | |
− | + | diazenyl)benzoic<br> acid</th> | |
− | + | <td colspan = "3"></td> | |
− | + | ||
− | + | </tr> | |
− | + | ||
− | + | ||
− | + | ||
− | + | <tr> | |
− | + | <th scope="row">Fraction 3</th> | |
− | + | <td colspan = 1.5>328,19</td> | |
− | + | <td colspan = 1.5>0,123</td> | |
− | + | <td colspan = 1.5>0,4</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Fraction 4</th> | |
− | + | <td colspan = 1.5>328,19</td> | |
− | + | <td colspan = 1.5>0,026</td> | |
− | + | <td colspan = 1.5>0,08</td> | |
− | + | </tr> | |
− | + | ||
− | + | ||
− | + | <tr> | |
− | + | <th scope="row">Description of product</th> | |
− | + | <td colspan = 3>Orange/brown solid</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
− | + | ||
</div> | </div> | ||
+ | <div class = "title"><p>NMR</p></div> | ||
+ | <p>Azofarbstoff Fraktion 3 1. Synthese | ||
+ | <br>NMR-Name: iGEM1 | ||
+ | <br><br>Azofarbstoff Fraktion(9)MeOH 1. Synthese | ||
+ | <br>NMR-Name: iGEM2</p> | ||
</div> | </div> | ||
+ | </div> | ||
<button class="read-more"> | <button class="read-more"> | ||
<i class="fa fa-angle-double-down"></i> | <i class="fa fa-angle-double-down"></i> | ||
</button> | </button> | ||
− | |||
</div> | </div> | ||
</div> | </div> | ||
+ | </div> | ||
</div> | </div> | ||
− | <div style="margin-top: 30%" class="timeline-block timeline-block-left"> | + | <div style = "margin-top: 30%"class="timeline-block timeline-block-left"> |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>14<br>Mar</p> | <p>14<br>Mar</p> | ||
Line 2,816: | Line 2,757: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>249,01</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>2,19</td> | |
− | + | <td>8,8</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Zn</th> | |
− | + | <td>65,38</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,46</td> | |
− | + | <td>22,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">NH<sub>4</sub>Cl</th> | |
− | + | <td>53,49</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,71</td> | |
− | + | <td>13,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | |
− | + | <td>270,29</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>6,89</td> | |
− | + | <td>25,5</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">2-methoxyethanol</th> | |
− | + | <td>76,09</td> | |
− | + | <td>0,97</td> | |
− | + | <td>60</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | |
− | + | <td>18,00/46,07</td> | |
− | + | <td>1,00/0,79</td> | |
− | + | <td>72</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo- 1-nitrobenzen (2,19 g; 8,8 mmol) was dissolved in 60 mL 2-methoxyethanol. | + | <p>4-Iodo- 1-nitrobenzen (2,19 g; 8,8 mmol) was dissolved in 60 mL 2-methoxyethanol. Zn dust |
− | + | (1,46 g; 22,3 mmol) and NH 4 Cl (0,71 g; 13,3 mmol) was added and the reaction mixture | |
− | + | was stirred at room temperature. The reaction was monitored by TLC (5:1 hexanes/EtOAc). | |
− | (1,46 g; 22,3 mmol) and NH 4 Cl (0,71 g; 13,3 mmol) was added and the reaction | + | After 50 minutes the solution was cooled to 0°C. FeCl 3 × 6 H 2 O (6,89 g; 25,5 mmol) was |
− | + | solved in 72 mL H 2 O/EtOH (5:1) and added to the reaction mixture which then was stirred 3 | |
− | was stirred at room temperature. The reaction was monitored by TLC (5:1 | + | hours at 0°C. Following the reaction mixture was extracted with EtOAc (3 × 80 mL), washed |
− | + | with brine and dried over MgSO 4 . The received solution was concentrated under reduced | |
− | After 50 minutes the solution was cooled to 0°C. FeCl 3 × 6 H 2 O (6,89 g; 25,5 | + | pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). The |
− | + | solvent was removed and the product 4-iodo- 1-nitrosobenzen (0,6 g; 2,6 mmol; 30%) was | |
− | solved in 72 mL H 2 O/EtOH (5:1) and added to the reaction mixture which then | + | |
− | + | ||
− | + | ||
− | hours at 0°C. Following the reaction mixture was extracted with EtOAc (3 × 80 | + | |
− | + | ||
− | + | ||
− | with brine and dried over MgSO 4 . The received solution was concentrated under | + | |
− | + | ||
− | pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). | + | |
− | + | ||
− | solvent was removed and the product 4-iodo- 1-nitrosobenzen (0,6 g; 2,6 mmol; | + | |
− | + | ||
− | + | ||
received as a green solid.</p> | received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p> | + | <div class = "title"><p>Yield: </p> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
<table class="table"> | <table class="table"> | ||
<thead> | <thead> | ||
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<tr> | <tr> | ||
<th scope="row">Yield</th> | <th scope="row">Yield</th> | ||
− | <td colspan=1.5>Literature: 82%</td> | + | <td colspan = 1.5>Literature: 82%</td> |
− | <td colspan=1.5>Practically: 30%</td> | + | <td colspan = 1.5>Practically: 30%</td> |
</tr> | </tr> | ||
<tr> | <tr> | ||
<th scope="row">Description of product</th> | <th scope="row">Description of product</th> | ||
− | <td colspan=3>Green solid</td> | + | <td colspan = 3>Green solid</td> |
</tr> | </tr> | ||
</tbody> | </tbody> | ||
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</div> | </div> | ||
</div> | </div> | ||
− | |||
<div class="timeline-block timeline-block-right"> | <div class="timeline-block timeline-block-right"> | ||
<div class="marker-right"> | <div class="marker-right"> | ||
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<div class="timeline-text biggerPicture"> | <div class="timeline-text biggerPicture"> | ||
<h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | <h3>Synthesis 3,5-bis((4-iodophenyl)diazenyl)benzoic acid</h3> | ||
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/d/d0/T--Franconia--Beam--acid.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>233,00</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,60</td> | |
− | + | <td>2,6</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>152,20</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,18</td> | |
− | + | <td>1,2</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Acetic acid</th> | |
− | + | <td>60,05</td> | |
− | + | <td>1,05</td> | |
− | + | <td>25</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>3,5-diaminobenzoic (0,18 g; 1,2 mmol) acid in 25 mL acetic acid was added to | + | <p>3,5-diaminobenzoic (0,18 g; 1,2 mmol) acid in 25 mL acetic acid was added to 4-iodo- 1- |
− | + | nitrosobenzene (0,60 g; 2,6 mmol). The reaction mixture was stirred at room temperature | |
− | + | ||
− | nitrosobenzene (0,60 g; 2,6 mmol). The reaction mixture was stirred at room | + | |
− | + | ||
for two nights. Following it was concentrated under reduced pressure. | for two nights. Following it was concentrated under reduced pressure. | ||
− | <br>¼ of the reaction mixture was purified via column chromatography (EtOH/DCM, | + | <br>¼ of the reaction mixture was purified via column chromatography (EtOH/DCM, 1:19). |
− | + | <br>¾ of the reaction mixture was washed with 5M NaOH and EtOAc. The aqueous phase was | |
− | <br>¾ of the reaction mixture was washed with 5M NaOH and EtOAc. The aqueous | + | |
− | + | ||
− | + | ||
acidifies with AcOH to pH 2. | acidifies with AcOH to pH 2. | ||
<br>Observation: Green solid precipitates and the organic phase was orange. | <br>Observation: Green solid precipitates and the organic phase was orange. | ||
Line 3,032: | Line 2,953: | ||
</div> | </div> | ||
− | <div style="margin-top: 30%" class="timeline-block timeline-block-left"> | + | <div style = "margin-top: 30%"class="timeline-block timeline-block-left"> |
<div class="marker-left"> | <div class="marker-left"> | ||
<p>13<br>Mar</p> | <p>13<br>Mar</p> | ||
Line 3,039: | Line 2,960: | ||
<div class="timeline-box"> | <div class="timeline-box"> | ||
<div class="timeline-text"> | <div class="timeline-text"> | ||
− | <h3>Synthesis 4-Iodo- 1-Nitrosobenzen</h3> | + | <h3>Synthesis 4-Iodo-1-Nitrosobenzen</h3> |
− | <div class="title"><p>Chemical equation:</p></div> | + | <div class = "title"><p>Chemical equation:</p></div> |
− | <img src="https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> | + | <img src = "https://static.igem.org/mediawiki/2017/a/a2/T--Franconia--Beam--nitrobenzen.png"> |
<div class="read-more-content"> | <div class="read-more-content"> | ||
− | <div class="title"><p>Reagents:</p></div> | + | <div class = "title"><p>Reagents:</p></div> |
− | <div class=table-responsive"> | + | <div class = table-responsive"> |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th></th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>ρ [g/cm<sup>3</sup>]</th> | |
− | + | <th>V [mL]</th> | |
− | + | <th>m [g]</th> | |
− | + | <th>n [mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzene</th> | |
− | + | <td>249,01</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>2,04</td> | |
− | + | <td>8,2</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Zn</th> | |
− | + | <td>65,38</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>1,24</td> | |
− | + | <td>19,0</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">NH<sub>4</sub>Cl</th> | |
− | + | <td>53,49</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>0,7</td> | |
− | + | <td>13,1</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">FeCl<sub>3</sub> × 6 H<sub>2</sub>O</th> | |
− | + | <td>270,29</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | <td>6,58</td> | |
− | + | <td>24,3</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">2-methoxyethanol</th> | |
− | + | <td>76,09</td> | |
− | + | <td>0,97</td> | |
− | + | <td>60</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">H<sub>2</sub>O/EtOH (5:1)</th> | |
− | + | <td>18,00/46,07</td> | |
− | + | <td>1,00/0,79</td> | |
− | + | <td>72</td> | |
− | + | <td>-</td> | |
− | + | <td>-</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
</div> | </div> | ||
− | <div class="title"><p>Procedure:</p></div> | + | <div class = "title"><p>Procedure:</p></div> |
− | <p>4-Iodo- 1-nitrobenzen (2,04 g; 8,2 mmol) was dissolved in 60 mL 2-methoxyethanol. | + | <p>4-Iodo- 1-nitrobenzen (2,04 g; 8,2 mmol) was dissolved in 60 mL 2-methoxyethanol. Zn dust |
− | + | (1,24 g; 19,0 mmol) and NH 4 Cl (0,7 g; 13,1 mmol) was added and the reaction mixture was | |
− | + | stirred at room temperature. The reaction was monitored by TLC (5:1 hexanes/EtOAc). | |
− | (1,24 g; 19,0 mmol) and NH 4 Cl (0,7 g; 13,1 mmol) was added and the reaction | + | After 45 minutes the solution was cooled to 0°C. FeCl 3 × 6 H 2 O (6,58 g; 24,3 mmol) was |
− | + | solved in 72 mL H 2 O/EtOH (5:1) and added to the reaction mixture which then was stirred 3 | |
− | stirred at room temperature. The reaction was monitored by TLC (5:1 | + | hours at 0°C. Following the reaction mixture was extracted with EtOAc (3 × 80 mL), washed |
− | + | with brine and dried over MgSO 4 . The received solution was concentrated under reduced | |
− | After 45 minutes the solution was cooled to 0°C. FeCl 3 × 6 H 2 O (6,58 g; 24,3 | + | pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). The |
− | + | solvent was removed and the product 4-iodo- 1-nitrosobenzen (0,863 g; 3,7 mmol; 45%) | |
− | solved in 72 mL H 2 O/EtOH (5:1) and added to the reaction mixture which then | + | |
− | + | ||
− | + | ||
− | hours at 0°C. Following the reaction mixture was extracted with EtOAc (3 × 80 | + | |
− | + | ||
− | + | ||
− | with brine and dried over MgSO 4 . The received solution was concentrated under | + | |
− | + | ||
− | pressure and purified by silica gel column chromatography (hexanes/EtOAc, 50:1). | + | |
− | + | ||
− | solvent was removed and the product 4-iodo- 1-nitrosobenzen (0,863 g; 3,7 mmol; | + | |
− | + | ||
was received as a green solid.</p> | was received as a green solid.</p> | ||
− | <div class="title"><p>Yield: </p></div> | + | <div class = "title"><p>Yield: </p></div> |
− | + | <div class = table-responsive"> | |
− | + | <table class="table"> | |
− | + | <thead> | |
− | + | <tr> | |
− | + | <th>Product</th> | |
− | + | <th>M [g/mol]</th> | |
− | + | <th>m[mg]</th> | |
− | + | <th>n[mmol]</th> | |
− | + | </tr> | |
− | + | </thead> | |
− | + | <tbody> | |
− | + | <tr> | |
− | + | <th scope="row">4-iodo-1-nitrosobenzen</th> | |
− | + | <td>233,0</td> | |
− | + | <td>0,863</td> | |
− | + | <td>3,7</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Yield</th> | |
− | + | <td colspan = 1.5>Literature: 82%</td> | |
− | + | <td colspan = 1.5>Practically: 45%</td> | |
− | + | </tr> | |
− | + | <tr> | |
− | + | <th scope="row">Description of product</th> | |
− | + | <td colspan = 3>Green solid</td> | |
− | + | </tr> | |
− | + | </tbody> | |
− | + | </table> | |
+ | </div> | ||
</div> | </div> | ||
− | |||
<button class="read-more"> | <button class="read-more"> | ||
<i class="fa fa-angle-double-down"></i> | <i class="fa fa-angle-double-down"></i> | ||
</button> | </button> | ||
+ | </div> | ||
</div> | </div> | ||
</div> | </div> | ||
</div> | </div> | ||
</div> | </div> | ||
+ | <div class="show-timeline-wrapper"> | ||
+ | <div class="show-timeline">Show Timeline</div> | ||
+ | </div> | ||
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Latest revision as of 23:06, 1 November 2017
Method 1
Protein Building Blocks
Protein building Blocks (without additional Streptavidin) . The single building blocks contain N- and C-terminal catcher-tag elements to form a permanent lock-key system. The polymer is build of two different building blocks as one single building block cannot be handled without instant polymerization. Mixing of the two building blocks start the polymerization via condensation reaction leading to a biopolymer tissue.
Pilis/Carbon Nano Tubes
Geobacter-conductive pili. The bacteria geobacter is a strictly anaerobic stem, which can produce electrically conductive proteins (Pili). Originally, they are used for their own energy gain however, they can also be used as conductive layer in our dielectric elastomer actuator and replace the carbon nanotubes as ecologically friendly alternative.
Carbon Nanotubes (CNTs) are tubular architectures made of pure carbon. Every single carbon atom is sp2 hybridized and arranged in a hexagonal pattern. One can distinguish between Single Walled Carbon Nanotubes (SWCNTs) and Multi Walled Carbon Nanotubes (MWCNTs). The fabrication of the tubes can either be achieved by laser ablation of graphite or with a catalyst in a carbon rich gas phase. As pure carbon material, they are light-weight and flexible and robust. Further their thermal and electric conductivity is highly remarkable.
Artificial Muscle
Dielectric Elastomer Actuators (DEAs) are made of alternating layers of elastic and conductive material e.g. CNTs forming a stacked capacitor. The top and bottom contacts are metallic electrodes. By application of a voltage the elastomer between the cathodes and anodes is compressed in z-dimension and expands in the x,y-plane. This leads to a muscle-like contraction of the whole system.
Method 2
Protein Building Blocks
Protein building Blocks (with additional Streptavidin). The single building blocks contain N- and C-terminal catcher-tag elements with a streptavidin in the center of the protein. The catcher-tag system binds a permanent lock-key system to each other. The streptavidin unit can bind to the biotin functionalized azo dye to integrate the molecules into the polymer tissue.
Azo Dye
Molecular Machines (Azo dyes) can fulfill motion on a molecular length scale. The contraction of the dye is driven by light, which changes the conformation of the -N=N- bond from trans to cis. Implemented in high number in a tissue they can lead to contraction of the whole tissue. The invention of such small motors was awarded the nobel prize in chemistry in 2016.
Artificial Muscle
Muscle tissue with molecular machines can be obtained by combining biopolymeric tissue with an integrated streptavidin moiety. The streptavidin can bind a biotin functionalized azo dye leading to a further cross-linking. Via light-irradiation the azo dye molecules change their conformation and contract the tissue. Thermal or irradiation with a longer wavelength restores the position of the azo dye and the tissue relaxes to the original state.
The work, which is and can be done by robots is continuously increasing as well as the number of steps where complex shaped matter has to be handled. For this purpose, soft robotics are essential to prevent damage from the material. Current materials for soft robotics are based on silicones and related polymeric materials. Combined with electrically conductive materials in alternating layers, they form dielectric elastomer actuators (DEAs), which serve as muscle in robot arms. Silicones and elastic polymers can be counted to rather cost-efficient materials. However, considering the production of the material a high amount of electricity and chemical effort must be applied. This can be circumvented by a production from E. coli, where the organism produces a economically friendly biopolymer with the desired properties. The biosynthesis of the polymer building blocks, safes a significant amount of resources and energy.
The fabrication of the silicones to a device is carried out under elevated temperatures, where high accuracy at a micrometer scale is a crucial factor. This accuracy must also be maintained for the device made of biopolymer, which can be realized with modern 3D printers. Further, the 3D-printer is operating under ambient conditions, which safes money in the fabrication process.
Due to the material properties, a special issue is the degradation of the biopolymer in dependence of time. A degradation of the material can mainly be circumvented by using the cell-free peptides, which prevents the consumption of the peptides by the cells. However, oxygen and mechanic stress are main issues, which have to be tackled. Oxygen can be excluded by instant packing of the material, whereas the mechanic durability of this material is still unknown. However, a comparison with a hydrogel polyacrylate based or a disposable DEA implies a lifetime of 100 to 2960 cycles.[1,2]
Biopolymer based DEA | Silicone based DEA | |
---|---|---|
Raw materials (price) | 6 € /g ink [3,4] | Av. 0,10 € /g ink[5] |
Fabrication | 3D printing | 3D aerosol jet printing @ 80°C[6] |
Solvent | Water | Isopropanol/terpineol[6] |
Weight | est. 1 g/mL (density of water) | 1.1-1.3 g/mL [7] |
Waste | Biodegradable polymer; Simple regain of conductive material | Recycling of silicone possible, regain of conductive material complex to achieve |
Timeline
Materials
Plasmids
- pBAD/Myc-His
- pSB1C3
Inserts/ constructs for pBAD/ Myc-His plasmid
- a) 3-Spytag-ELP5-HisTag (to be cut with NcoI and XhoI)
- a) Spytag-Streptavidin-ELP5-SnoopCatcher (to be cut with XhoI and HindIII-HF)
- a) HisTag-Snooptag-ELP5-Spycatcher (to be cut with XhoI and HindIII-HF)
- a) Kationisch kurz (to be cut with NcoI and XhoI)
- a) Anionisch kurz (to be cut with NcoI and XhoI)
- a) W51W54 (to be cut with HindIII-HF and BssHII)
Inserts/ constructs for pSB1C3 plasmid
- b) 3-Spytag-ELP5-HisTag (to be cut with EcoRI and PstI)
- b) Spytag-Streptavidin-ELP5-SnoopCatcher (to be cut with EcoRI and PstI)
- b) HisTag-Snooptag-ELP5-Spycatcher (to be cut with EcoRI and PstI)
- b) Kationisch kurz (to be cut with EcoRI and PstI)
- b) Anionisch kurz (to be cut with EcoRI and PstI)
- b) W51W54 (to be cut with EcoRI and PstI)
Timeline
The term “molecular machine” refers to a system that is able to perform mechanical movement on a nanoscopic scale by application of an external stimulus. In order to do so, such systems only consist of a small number of molecules. Depending on the nature of the used molecules, possible stimuli can be electrical energy (redox changes), electromagnetic energy (light) or chemical energy (change of pH value or addition of specific ions). Being an exceptionally novel field of science, starting in the mid 1980’s and just being rewarded with the Nobel prize of chemistry in 2016, the current applications of molecular machines are still rather few. However, a multitude of possible applications are being explored by the minute. Many mechanical devices can be mimicked, including rotors, oscillators, gears, paddle wheels, turnstiles, brakes, ratchets and gyroscopes.[1] One example of a more sophisticated system is a molecular motor[2] that can perform a 360° rotation by subsequent application of light and temperature, as can be seen in Figure 1. In another research group, four similar rotary systems have been combined on a larger molecule in order to create a four-wheeled nano-car that was able to move over a surface upon irradiation.[3]
In this project, azo dyes are used as molecular machines. Upon irradiation, the -N=N- azo group changes from a trans configuration to a cis configuration. As a consequence, the distance between the substituents R is shortened, resulting in a muscle-like contraction. The working principle of azo dyes as molecular machines can be seen in Figure 2.
References: [1] V. Balzani, A. Credi, M. Venturi: Molecular Devices and Machines – A Journey into the Nano World, Wiley-VCH, Weinheim, 2003.
[2] N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature, 1999, 401, 152-155.
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DEAs, or dielectric elastomer actuators, generally consist of thin elastic films coated with compliant electrode material on two opposing phases. That makes them flexible plate capacitors that deform due to Maxwell stress when applying a voltage across the electrodes. Since the elastic material is incompressible, applying said voltage causes the reduction of the film in thickness to result in an expansion in area. Stacking and bundling of multiple DEAs allows an actuation system to be adapted to different loading scenarios.Several materials are suitable for manufacturing DEAs. Electrodes can be made e.g. of metals, polymers, graphite or carbon nano tubes. Elastic dielectric materials in use for industrial applications are Polyacryl, Polyurethane or Polysiloxane. This project however focusses on the synthesis of a catcher-tag polymer as dielectric medium while using carbon nano tubes for the electrodes.
Manufacturing DEAs is possible in multiple ways. Thereby dipping, spin-coating and casting techniques are widely spread. For biomaterials, cartridges are more suitable for handling and dispensing the dielectric material. For the application of electrodes onto the elastomer, sputter and spraying techniques are widely used within the industry. Another option is the selective wetting process based on water-based solutions for when the polymer material is hydrophobic.
References: F. Nendel, S. Reitelshöfer: Conception of an infrastructure for the volumetric flow rate controlled supply of process gases and for the dynamic diversion of aerosol-flows for manufacturing flexible graphene electrodes. Institute for Factory Automation and Production Systems, (06/2017)