学术探索
学术期刊
学术作者
新闻热点
数据分析
智能评审

Visible-Light Initiated Thiol-Michael Addition Photopolymerization Reactions

被引：76
作者：
Chatani, Shunsuke [1 ]
Gong, Tao [1 ]
Earle, Brittany A. [1 ]
Podgorski, Maciej [1 ,2 ]
Bowman, Christopher N. [1 ]
机构：
[1] Univ Colorado, Dept Chem & Biol Engn, Boulder, CO 80309 USA
[2] MCS Univ, Dept Polymer Chem, Fac Chem, PL-20031 Lublin, Poland
来源：
ACS MACRO LETTERS | 2014年 / 3卷 / 04期
基金：
美国国家科学基金会;
关键词：
CLICK REACTIONS; CUAAC REACTION; ENE; POLYMERIZATION; CHEMISTRY; AMINE;
D O I：
10.1021/mz500132j
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 [高分子化学与物理];
摘要：
A visible-light base generating system was successfully employed in catalyzing the thiol-Michael addition reaction to yield cross-linked polymers from a stoichiometric mixture of model thiol and vinyl monomers. Implementation of the radical inhibitor TEMPO with a combination of a photosensitizer (isopropylthioxanthone, ITX) and a photobase generator (triazabicyclodecene tetraphenylborate, TBD center dot HBPh4) resulted in suppression of radical mediated side reactions and provided stoichiometric and complete conversion of both thiol and vinyl functional groups. The new initiating system acts as an efficient visible-light photobase generator that improves the orthogonality of the thiol-Michael addition with respect to off-stoichiometric radical thiol-vinyl addition/vinyl chain reactions. This approach opens up a variety of possibilities for base-catalyzed reactions in multiple applications such as coatings and biomaterials that require biocompatible, environmentally friendly, and low-energy visible-light initiation.
引用
收藏
页码：315 / 318
页数：4
相关论文
共 21 条
[1]
Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction [J].
Adzima, Brian J. ;
Tao, Youhua ;
Kloxin, Christopher J. ;
DeForest, Cole A. ;
Anseth, Kristi S. ;
Bowman, Christopher N. .
NATURE CHEMISTRY, 2011, 3 (03) :256-259
[2]
Nucleophile-Initiated Thiol-Michael Reactions: Effect of Organocatalyst, Thiol, and Ene [J].
Chan, Justin W. ;
Hoyle, Charles E. ;
Lowe, Andrew B. ;
Bowman, Mark .
MACROMOLECULES, 2010, 43 (15) :6381-6388
[3]
The nucleophilic, phosphine-catalyzed thiol-ene click reaction and convergent star synthesis with RAFT-prepared homopolymers [J].
Chan, Justin W. ;
Yu, Bing ;
Hoyle, Charles E. ;
Lowe, Andrew B. .
POLYMER, 2009, 50 (14) :3158-3168
[4]
Relative reactivity and selectivity of vinyl sulfones and acrylates towards the thiol-Michael addition reaction and polymerization [J].
Chatani, Shunsuke ;
Nair, Devatha P. ;
Bowman, Christopher N. .
POLYMER CHEMISTRY, 2013, 4 (04) :1048-1055
[5]
Advancements in photoinitiators -: Opening up new applications for radiation curing [J].
Dietliker, K. ;
Huesler, R. ;
Birbaum, J. -L. ;
Ilg, S. ;
Villeneuve, S. ;
Studer, K. ;
Jung, T. ;
Benkhoff, J. ;
Kura, H. ;
Matsumoto, A. ;
Oka, H. .
PROGRESS IN ORGANIC COATINGS, 2007, 58 (2-3) :146-157
[6]
A novel copper containing photoinitiator, copper(II) acylphosphinate, and its application in both the photomediated CuAAC reaction and in atom transfer radical polymerization [J].
Gong, Tao ;
Adzima, Brian J. ;
Bowman, Christopher N. .
CHEMICAL COMMUNICATIONS, 2013, 49 (72) :7950-7952
[7]
Photopolymerization Reactions Using the Photoinitiated Copper (I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Reaction [J].
Gong, Tao ;
Adzima, Brian J. ;
Baker, Noah H. ;
Bowman, Christopher N. .
ADVANCED MATERIALS, 2013, 25 (14) :2024-2028
[8]
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis [J].
Hoyle, Charles E. ;
Lowe, Andrew B. ;
Bowman, Christopher N. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1355-1387
[9]
Thiol-Ene Click Chemistry [J].
Hoyle, Charles E. ;
Bowman, Christopher N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1540-1573
[10]
Thiol-epoxy/thiol-acrylate hybrid materials synthesized by photopolymerization [J].
Jian, Yu ;
He, Yong ;
Sun, Yukun ;
Yang, Haitao ;
Yang, Wantai ;
Nie, Jun .
JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (29) :4481-4489
123