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Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition
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| Zeitschriftentitel: | Journal of Polymer Science Part A: Polymer Chemistry |
|---|---|
| Personen und Körperschaften: | , , |
| In: | Journal of Polymer Science Part A: Polymer Chemistry, 52, 2014, 21, S. 3134-3141 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
|
| Schlagwörter: |
| author_facet |
Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. |
|---|---|
| author |
Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. |
| spellingShingle |
Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. Journal of Polymer Science Part A: Polymer Chemistry Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition Materials Chemistry Organic Chemistry Polymers and Plastics |
| author_sort |
isaacman, michael j. |
| spelling |
Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. 0887-624X 1099-0518 Wiley Materials Chemistry Organic Chemistry Polymers and Plastics http://dx.doi.org/10.1002/pola.27371 <jats:title>ABSTRACT</jats:title><jats:p>Nitrile oxide 1,3 dipolar cycloaddition is a simple and powerful coupling methodology. However, the self‐dimerization of nitrile oxides has prevented the widespread use of this strategy for macromolecular coupling. By combining an <jats:italic>in situ</jats:italic> nitrile oxide generation with a highly reactive activated dipolarophile, we have overcome these obstacles and present a metal‐free macromolecular coupling strategy for the modular synthesis of several ABA triblock copolymers. Nitrile oxides were generated <jats:italic>in situ</jats:italic> from chloroxime terminated poly(dimethylsiloxane) B‐blocks and coupled with several distinct hydrophilic (poly(2‐methyloxazoline) and poly(ethylene glycol)), and poly(<jats:italic>N</jats:italic>‐isopropylacrylamide) or hydrophobic (poly(<jats:sc>l</jats:sc>‐lactide) A‐blocks terminated in activated dipolarophiles in a rapid fashion with high yield. This methodology overcomes many drawbacks of previously reported metal‐free methods due to its rapid kinetics, versatility, scalability, and ease of introduction of necessary functionality. Nitrile oxide cycloaddition should find use as an attractive macromolecular coupling strategy for the synthesis of biocompatible polymeric nanostructures. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <jats:bold>2014</jats:bold>, <jats:italic>52</jats:italic>, 3134–3141</jats:p> Rapid metal‐free macromolecular coupling via <i>In Situ</i> nitrile oxide‐activated alkene cycloaddition Journal of Polymer Science Part A: Polymer Chemistry |
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Journal of Polymer Science Part A: Polymer Chemistry |
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| title |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_unstemmed |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_full |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_fullStr |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_full_unstemmed |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_short |
Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_sort |
rapid metal‐free macromolecular coupling via <i>in situ</i> nitrile oxide‐activated alkene cycloaddition |
| topic |
Materials Chemistry Organic Chemistry Polymers and Plastics |
| url |
http://dx.doi.org/10.1002/pola.27371 |
| publishDate |
2014 |
| physical |
3134-3141 |
| description |
<jats:title>ABSTRACT</jats:title><jats:p>Nitrile oxide 1,3 dipolar cycloaddition is a simple and powerful coupling methodology. However, the self‐dimerization of nitrile oxides has prevented the widespread use of this strategy for macromolecular coupling. By combining an <jats:italic>in situ</jats:italic> nitrile oxide generation with a highly reactive activated dipolarophile, we have overcome these obstacles and present a metal‐free macromolecular coupling strategy for the modular synthesis of several ABA triblock copolymers. Nitrile oxides were generated <jats:italic>in situ</jats:italic> from chloroxime terminated poly(dimethylsiloxane) B‐blocks and coupled with several distinct hydrophilic (poly(2‐methyloxazoline) and poly(ethylene glycol)), and poly(<jats:italic>N</jats:italic>‐isopropylacrylamide) or hydrophobic (poly(<jats:sc>l</jats:sc>‐lactide) A‐blocks terminated in activated dipolarophiles in a rapid fashion with high yield. This methodology overcomes many drawbacks of previously reported metal‐free methods due to its rapid kinetics, versatility, scalability, and ease of introduction of necessary functionality. Nitrile oxide cycloaddition should find use as an attractive macromolecular coupling strategy for the synthesis of biocompatible polymeric nanostructures. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <jats:bold>2014</jats:bold>, <jats:italic>52</jats:italic>, 3134–3141</jats:p> |
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| author | Isaacman, Michael J., Cui, Weibin, Theogarajan, Luke S. |
| author_facet | Isaacman, Michael J., Cui, Weibin, Theogarajan, Luke S., Isaacman, Michael J., Cui, Weibin, Theogarajan, Luke S. |
| author_sort | isaacman, michael j. |
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| description | <jats:title>ABSTRACT</jats:title><jats:p>Nitrile oxide 1,3 dipolar cycloaddition is a simple and powerful coupling methodology. However, the self‐dimerization of nitrile oxides has prevented the widespread use of this strategy for macromolecular coupling. By combining an <jats:italic>in situ</jats:italic> nitrile oxide generation with a highly reactive activated dipolarophile, we have overcome these obstacles and present a metal‐free macromolecular coupling strategy for the modular synthesis of several ABA triblock copolymers. Nitrile oxides were generated <jats:italic>in situ</jats:italic> from chloroxime terminated poly(dimethylsiloxane) B‐blocks and coupled with several distinct hydrophilic (poly(2‐methyloxazoline) and poly(ethylene glycol)), and poly(<jats:italic>N</jats:italic>‐isopropylacrylamide) or hydrophobic (poly(<jats:sc>l</jats:sc>‐lactide) A‐blocks terminated in activated dipolarophiles in a rapid fashion with high yield. This methodology overcomes many drawbacks of previously reported metal‐free methods due to its rapid kinetics, versatility, scalability, and ease of introduction of necessary functionality. Nitrile oxide cycloaddition should find use as an attractive macromolecular coupling strategy for the synthesis of biocompatible polymeric nanostructures. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <jats:bold>2014</jats:bold>, <jats:italic>52</jats:italic>, 3134–3141</jats:p> |
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| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
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| spelling | Isaacman, Michael J. Cui, Weibin Theogarajan, Luke S. 0887-624X 1099-0518 Wiley Materials Chemistry Organic Chemistry Polymers and Plastics http://dx.doi.org/10.1002/pola.27371 <jats:title>ABSTRACT</jats:title><jats:p>Nitrile oxide 1,3 dipolar cycloaddition is a simple and powerful coupling methodology. However, the self‐dimerization of nitrile oxides has prevented the widespread use of this strategy for macromolecular coupling. By combining an <jats:italic>in situ</jats:italic> nitrile oxide generation with a highly reactive activated dipolarophile, we have overcome these obstacles and present a metal‐free macromolecular coupling strategy for the modular synthesis of several ABA triblock copolymers. Nitrile oxides were generated <jats:italic>in situ</jats:italic> from chloroxime terminated poly(dimethylsiloxane) B‐blocks and coupled with several distinct hydrophilic (poly(2‐methyloxazoline) and poly(ethylene glycol)), and poly(<jats:italic>N</jats:italic>‐isopropylacrylamide) or hydrophobic (poly(<jats:sc>l</jats:sc>‐lactide) A‐blocks terminated in activated dipolarophiles in a rapid fashion with high yield. This methodology overcomes many drawbacks of previously reported metal‐free methods due to its rapid kinetics, versatility, scalability, and ease of introduction of necessary functionality. Nitrile oxide cycloaddition should find use as an attractive macromolecular coupling strategy for the synthesis of biocompatible polymeric nanostructures. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <jats:bold>2014</jats:bold>, <jats:italic>52</jats:italic>, 3134–3141</jats:p> Rapid metal‐free macromolecular coupling via <i>In Situ</i> nitrile oxide‐activated alkene cycloaddition Journal of Polymer Science Part A: Polymer Chemistry |
| spellingShingle | Isaacman, Michael J., Cui, Weibin, Theogarajan, Luke S., Journal of Polymer Science Part A: Polymer Chemistry, Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition, Materials Chemistry, Organic Chemistry, Polymers and Plastics |
| title | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_full | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_fullStr | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_full_unstemmed | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_short | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| title_sort | rapid metal‐free macromolecular coupling via <i>in situ</i> nitrile oxide‐activated alkene cycloaddition |
| title_unstemmed | Rapid metal‐free macromolecular coupling via In Situ nitrile oxide‐activated alkene cycloaddition |
| topic | Materials Chemistry, Organic Chemistry, Polymers and Plastics |
| url | http://dx.doi.org/10.1002/pola.27371 |