Thiol–epoxy ‘click’ polymerization: efficient construction of reactive and functional polymers

The thiol–epoxy ‘click’ process is employed as a polymerization reaction to prepare linear polymer chains substituted with free hydroxyl groups. Post-polymerization modification of the hydroxyl units afforded functional polymers exhibiting substituent dependent properties. In this way, functionalized macromolecules are obtained in two simple synthetic steps from commercially available monomer building blocks and reagents.

[1]  Anzar Khan,et al.  A general synthetic strategy to prepare poly(ethylene glycol)-based multifunctional copolymers , 2012 .

[2]  H. Schlaad,et al.  A versatile polypeptoid platform based on N-allyl glycine. , 2012, Chemical communications.

[3]  S. Hvilsted Facile design of biomaterials by ‘click’ chemistry , 2012 .

[4]  A. Sanyal,et al.  Double click reaction strategies for polymer conjugation and post-functionalization of polymers , 2012 .

[5]  Anzar Khan,et al.  Efficient synthesis of multifunctional polymers via thiol-epoxy "click" chemistry. , 2012, Chemical communications.

[6]  B. Weckhuysen,et al.  On the Polymerization Behavior of Telomers: Metathesis versus Thiol–Ene Chemistry , 2012 .

[7]  A. Sanyal,et al.  Discrete macromolecular constructs via the Diels–Alder “Click” reaction , 2011 .

[8]  T. P. Davis,et al.  Macromolecular thiolysis of oxiranes: end-group modification of RAFT prepared homopolymers , 2011 .

[9]  B. Tang,et al.  Click Polymerization: Progresses, Challenges, and Opportunities , 2010 .

[10]  A. Lowe,et al.  Thiol-Based ‘Click’ Chemistries in Polymer Synthesis and Modification , 2010 .

[11]  A. Sanyal Diels–Alder Cycloaddition‐Cycloreversion: A Powerful Combo in Materials Design , 2010 .

[12]  É. Drockenmuller,et al.  Solving the loss of orthogonality during the polyaddition of α‐azide‐ω‐alkyne monomers catalyzed by Cu(PPh3)3Br: Application to the synthesis of high‐molar mass polytriazoles , 2010 .

[13]  C. Bowman,et al.  Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis. , 2010, Chemical Society reviews.

[14]  J. Pascault,et al.  Copper-Catalyzed vs Thermal Step Growth Polymerization of Starch-Derived α-Azide−ω-Alkyne Dianhydrohexitol Stereoisomers: To Click or Not To Click? , 2010 .

[15]  B. Sumerlin,et al.  Macromolecular Engineering through Click Chemistry and Other Efficient Transformations , 2010 .

[16]  Daniel J. Burke,et al.  Applications of orthogonal "click" chemistries in the synthesis of functional soft materials. , 2009, Chemical reviews.

[17]  C. Barner‐Kowollik,et al.  Has Click Chemistry Lead to a Paradigm Shift in Polymer Material Design , 2009 .

[18]  J. Pascault,et al.  Click chemistry step growth polymerization of novel alpha-azide-omega-alkyne monomers. , 2008, Chemical communications.

[19]  Jeffrey W Stansbury,et al.  Evaluation and Control of Thiol-ene/Thiol-epoxy Hybrid Networks. , 2007, Polymer.

[20]  C. Hawker,et al.  Orthogonal approaches to the simultaneous and cascade functionalization of macromolecules using click chemistry. , 2005, Journal of the American Chemical Society.

[21]  Craig J. Hawker,et al.  The Convergence of Synthetic Organic and Polymer Chemistries , 2005, Science.

[22]  Philipp Holzer,et al.  Click chemistry in materials synthesis. 1. Adhesive polymers from copper‐catalyzed azide‐alkyne cycloaddition , 2004 .

[23]  M. G. Finn,et al.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions. , 2001, Angewandte Chemie.

[24]  Robert Langer,et al.  Degradable Poly(β-amino esters): Synthesis, Characterization, and Self-Assembly with Plasmid DNA , 2000 .

[25]  M. E. Buck,et al.  Azlactone-Functionalized Polymers as Reactive Platforms for the Design of Advanced Materials: Progress in the Last Ten Years. , 2012, Polymer chemistry.

[26]  B. Tang,et al.  Azide-alkyne click polymerization: An update , 2011, Chinese Journal of Polymer Science.

[27]  Harm-Anton Klok,et al.  Synthesis of functional polymers by post-polymerization modification. , 2009, Angewandte Chemie.