Visible Light Photocatalytic Thiol–Ene Reaction: An Elegant Approach for Fast Polymer Postfunctionalization and Step-Growth Polymerization

作者: Jiangtao Xu , Cyrille Boyer

DOI: 10.1021/MA502460T

关键词: PolymerizationChemistryAlkeneAddition reactionAddition polymerPolymerReaction rateThiol-ene reactionStep-growth polymerizationPhotochemistry

摘要: An elegant approach for fast polymer postfunctionalization and step-growth polymerization (via addition reaction) under aerobic condition was developed from visible light photocatalytic thiol–ene “click” reaction, employing Ru(bpy)3Cl2 as photoredox catalyst p-toluidine redox mediator. The nature of the catalysts, thiol substrates, solvents were extensively investigated this reaction with two types alkene polymers: polybutadiene poly(allyl methacrylate)s. use N-methyl-2-pyrrolidone solvent mediator remarkably improved rates limited formation side products. Finally, highly efficient employed synthesis polymers by polymerization.

参考文章(90)
Xianglong Hu, Jie Tian, Tao Liu, Guoying Zhang, Shiyong Liu, Photo-Triggered Release of Caged Camptothecin Prodrugs from Dually Responsive Shell Cross-Linked Micelles Macromolecules. ,vol. 46, pp. 6243- 6256 ,(2013) , 10.1021/MA400691J
Taylor Ware, Abby R. Jennings, Zahra S. Bassampour, Dustin Simon, David Y. Son, Walter Voit, Degradable, silyl ether thiol–ene networks RSC Advances. ,vol. 4, pp. 39991- 40002 ,(2014) , 10.1039/C4RA06997H
Chih-Yen Huang, Yuhlong Oliver Su, Spectral and redox properties of zinc porphyrin core dendrimers with triarylamines as dendron Dalton Transactions. ,vol. 39, pp. 8306- 8312 ,(2010) , 10.1039/C0DT00199F
John D. Nguyen, Joseph W. Tucker, Marlena D. Konieczynska, Corey R. J. Stephenson, Intermolecular atom transfer radical addition to olefins mediated by oxidative quenching of photoredox catalysts. Journal of the American Chemical Society. ,vol. 133, pp. 4160- 4163 ,(2011) , 10.1021/JA108560E
Tehshik P. Yoon, Michael A. Ischay, Juana Du, Visible light photocatalysis as a greener approach to photochemical synthesis Nature Chemistry. ,vol. 2, pp. 527- 532 ,(2010) , 10.1038/NCHEM.687
Sebastiaan A. van den Berg, Jing Tu, Karen M. Sliedregt, Alexander Kros, Tom Wennekes, Han Zuilhof, Clickable Mesoporous Silica via Functionalization with 1,ω-Alkenes Advanced Materials Interfaces. ,vol. 1, pp. 1300061- ,(2014) , 10.1002/ADMI.201300061
Woo Jin Chung, Jared J. Griebel, Eui Tae Kim, Hyunsik Yoon, Adam G. Simmonds, Hyun Jun Ji, Philip T. Dirlam, Richard S. Glass, Jeong Jae Wie, Ngoc A. Nguyen, Brett W. Guralnick, Jungjin Park, Árpád Somogyi, Patrick Theato, Michael E. Mackay, Yung-Eun Sung, Kookheon Char, Jeffrey Pyun, The use of elemental sulfur as an alternative feedstock for polymeric materials Nature Chemistry. ,vol. 5, pp. 518- 524 ,(2013) , 10.1038/NCHEM.1624
Matthew J. Kade, Daniel J. Burke, Craig J. Hawker, The power of thiol‐ene chemistry Journal of Polymer Science Part A. ,vol. 48, pp. 743- 750 ,(2010) , 10.1002/POLA.23824
Lisa A. Sawicki, April M. Kloxin, Design of thiol–ene photoclick hydrogels using facile techniques for cell culture applications Biomaterials Science. ,vol. 2, pp. 1612- 1626 ,(2014) , 10.1039/C4BM00187G
Mariola Calle, Gerard Lligadas, Juan C. Ronda, Marina Galià, Virginia Cádiz, An efficient nonisocyanate route to polyurethanes via thiol‐ene self‐addition Journal of Polymer Science Part A. ,vol. 52, pp. 3017- 3025 ,(2014) , 10.1002/POLA.27347