A New Methodology for Assessing Macromolecular Click Reactions and Its Application to Amine–Tertiary Isocyanate Coupling for Polymer Ligation
Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term “click” is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true “click” reaction. With the purpose of providing a universal way to...
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| Published in: | Journal of the American Chemical Society Vol. 138; no. 12; pp. 4061 - 4068 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
WASHINGTON
American Chemical Society
30.03.2016
Amer Chemical Soc |
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| ISSN: | 0002-7863, 1520-5126, 1520-5126 |
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| Abstract | Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term “click” is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true “click” reaction. With the purpose of providing a universal way to benchmark polymer–polymer coupling efficiency at equimolarity and thus evaluate the fulfilment of click criteria, we report a simple one-pot methodology involving the homodicoupling of α-end-functionalized polymers using a small-molecule bifunctional linker. A combination of SEC analysis and chromatogram deconvolution enables straightforward quantification of the coupling efficiency. We subsequently employ this methodology to evaluate an overlooked candidate for the click reaction family: the addition of primary amines to α-tertiary isocyanates (α- t NCO). Using our bifunctional linker coupling strategy, we show that the amine– t NCO reaction fulfills the criteria for a polymer–polymer click reaction, achieving rapid, chemoselective, and quantitative coupling at room temperature without generating any byproducts. We demonstrate that amine– t NCO coupling is faster and more efficient than the more common amine–tertiary active ester coupling under equivalent conditions. Additionally, we show that the α- t NCO end group is unprecedentedly stable in aqueous media. Thus, we propose that the amine– t NCO ligation is a powerful new click reaction for efficient macromolecular coupling. |
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| AbstractList | Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term "click" is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true "click" reaction. With the purpose of providing a universal way to benchmark polymer-polymer coupling efficiency at equimolarity and thus evaluate the fulfilment of click criteria, we report a simple one-pot methodology involving the homodicoupling of α-end-functionalized polymers using a small-molecule bifunctional linker. A combination of SEC analysis and chromatogram deconvolution enables straightforward quantification of the coupling efficiency. We subsequently employ this methodology to evaluate an overlooked candidate for the click reaction family: the addition of primary amines to α-tertiary isocyanates (α-(t)NCO). Using our bifunctional linker coupling strategy, we show that the amine-(t)NCO reaction fulfills the criteria for a polymer-polymer click reaction, achieving rapid, chemoselective, and quantitative coupling at room temperature without generating any byproducts. We demonstrate that amine-(t)NCO coupling is faster and more efficient than the more common amine-tertiary active ester coupling under equivalent conditions. Additionally, we show that the α-(t)NCO end group is unprecedentedly stable in aqueous media. Thus, we propose that the amine-(t)NCO ligation is a powerful new click reaction for efficient macromolecular coupling. Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term "click" is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true "click" reaction. With the purpose of providing a universal way to benchmark polymer-polymer coupling efficiency at equimolarity and thus evaluate the fulfilment of click criteria, we report a simple one-pot methodology involving the homodicoupling of α-end-functionalized polymers using a small-molecule bifunctional linker. A combination of SEC analysis and chromatogram deconvolution enables straightforward quantification of the coupling efficiency. We subsequently employ this methodology to evaluate an overlooked candidate for the click reaction family: the addition of primary amines to α-tertiary isocyanates (α-(t)NCO). Using our bifunctional linker coupling strategy, we show that the amine-(t)NCO reaction fulfills the criteria for a polymer-polymer click reaction, achieving rapid, chemoselective, and quantitative coupling at room temperature without generating any byproducts. We demonstrate that amine-(t)NCO coupling is faster and more efficient than the more common amine-tertiary active ester coupling under equivalent conditions. Additionally, we show that the α-(t)NCO end group is unprecedentedly stable in aqueous media. Thus, we propose that the amine-(t)NCO ligation is a powerful new click reaction for efficient macromolecular coupling.Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term "click" is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true "click" reaction. With the purpose of providing a universal way to benchmark polymer-polymer coupling efficiency at equimolarity and thus evaluate the fulfilment of click criteria, we report a simple one-pot methodology involving the homodicoupling of α-end-functionalized polymers using a small-molecule bifunctional linker. A combination of SEC analysis and chromatogram deconvolution enables straightforward quantification of the coupling efficiency. We subsequently employ this methodology to evaluate an overlooked candidate for the click reaction family: the addition of primary amines to α-tertiary isocyanates (α-(t)NCO). Using our bifunctional linker coupling strategy, we show that the amine-(t)NCO reaction fulfills the criteria for a polymer-polymer click reaction, achieving rapid, chemoselective, and quantitative coupling at room temperature without generating any byproducts. We demonstrate that amine-(t)NCO coupling is faster and more efficient than the more common amine-tertiary active ester coupling under equivalent conditions. Additionally, we show that the α-(t)NCO end group is unprecedentedly stable in aqueous media. Thus, we propose that the amine-(t)NCO ligation is a powerful new click reaction for efficient macromolecular coupling. Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term "click" is often applied inaccurately to polymer ligation reactions that fail to respect the criteria that typify a true "click" reaction. With the purpose of providing a universal way to benchmark polymer polymer coupling efficiency at equimolarity and thus evaluate the fulfilment of click criteria, we report a simple one-pot methodology involving the homodicoupling of alpha-end-functionalized polymers using a small-molecule bifunctional linker. A combination of SEC analysis and chromatogram deconvolution enables straightforward quantification of the coupling efficiency. We subsequently employ this methodology to evaluate an overlooked candidate for the click reaction family: the addition of primary amines to alpha-tertiary isocyanates (alpha-(NCO)-N-t). Using our bifunctional linker coupling strategy, we show that the amine-(NCO)-N-t reaction fulfills the criteria for a polymer polymer click reaction, achieving rapid, chemoselective, and quantitative coupling at room temperature without generating any byproducts. We demonstrate that amine-(NCO)-N-t coupling is faster and more efficient than the more common amine tertiary active ester coupling under equivalent conditions. Additionally, we show that the alpha-(NCO)-N-t end group is unprecedentedly stable in aqueous media. Thus, we propose that the amine-(NCO)-N-t ligation is a powerful new click reaction for efficient macromolecular coupling. |
| Author | Perrier, Sébastien Gody, Guillaume Roberts, Derrick A Maschmeyer, Thomas |
| AuthorAffiliation | Department of Chemistry The University of Cambridge The University of Sydney Monash University The University of Warwick Laboratory of Advanced Catalysis for Sustainability, School of Chemistry Faculty of Pharmacy and Pharmaceutical Sciences |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Laboratory of Advanced Catalysis for Sustainability, School of Chemistry – name: The University of Warwick – name: Faculty of Pharmacy and Pharmaceutical Sciences – name: Monash University – name: The University of Sydney – name: The University of Cambridge |
| Author_xml | – sequence: 1 givenname: Guillaume surname: Gody fullname: Gody, Guillaume email: g.gody@warwick.ac.uk – sequence: 2 givenname: Derrick A surname: Roberts fullname: Roberts, Derrick A – sequence: 3 givenname: Thomas surname: Maschmeyer fullname: Maschmeyer, Thomas – sequence: 4 givenname: Sébastien surname: Perrier fullname: Perrier, Sébastien email: s.perrier@warwick.ac.uk |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26927624$$D View this record in MEDLINE/PubMed |
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| Keywords | FUNCTIONALIZED POLYMERS CONJUGATION FULL MONOMER CONVERSION BLOCK-COPOLYMERS FRAGMENTATION CHAIN TRANSFER CROSS-LINKING CHEMISTRY RADICAL POLYMERIZATION MODULAR SYNTHESIS RAFT POLYMERIZATION |
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| Snippet | Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term “click” is often applied inaccurately to... Click reactions have provided access to an array of remarkably complex polymer architectures. However, the term "click" is often applied inaccurately to... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | A New Methodology for Assessing Macromolecular Click Reactions and Its Application to Amine–Tertiary Isocyanate Coupling for Polymer Ligation |
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