Marriage of ring-opening metathesis polymerization and thiolmaleimide chemistries: Direct polymerization of prefunctionalized monomers or postpolymerization modification?

被引:9
作者
Li, Zi-Long [1 ]
Zeng, Fu-Rong [1 ]
Li, Hao-Cheng [1 ]
Zeng, Wei-Li [1 ]
Cai, Hang-Chang [1 ]
Jiang, Hong [1 ]
机构
[1] Huazhong Agr Univ, Coll Sci, Dept Chem, Wuhan 430070, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
Ring-opening metathesis polymerization; Thiol-maleimide chemistries; Postpolymerization modification; THIOL-ENE CLICK; STEP-GROWTH POLYMERIZATION; POST-FUNCTIONALIZATION; DENDRONIZED POLYMERS; MACROMONOMER APPROACH; MICHAEL CHEMISTRY; ROMP POLYMERS; LIVING ROMP; COPOLYMERS; HYDROGELS;
D O I
10.1016/j.polymer.2017.06.018
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Two distinct synthetic methodologies to furnish polynorbornene bearing thiol-maleimide adduct side groups, namely direct ring-opening metathesis polymerization (ROMP) of prefunctionalized monomers and postpolymerization modification, were investigated and compared in this study. ROMP of thiolmaleimide adduct-containing monomers M1-M4 was performed to yield polymers PM1-PM4 with full conversion of monomers but broad molecular weight distribution. Meanwhile, narrowly distributed polymers P1-P4 were generated through postpolymerization modification of polymer P0 by using thiolmaleimide reaction. However, removal of residual monomer M0 was an indispensable step prior to postpolymerization modification since incomplete monomer conversion was observed in the previous step, synthesis of polymer P0 using ROMP of maleimide-containing monomer M0. Narrow molecular weight distribution in conjunction with good polymerization controllability renders the strategy of postpolymerization modification a seemingly more reliable synthetic protocol to achieve the goal of this contribution. Finally, polymers P0-P4 were subjected to property studies to elucidate their thermal stability, glass transition behavior, wettability and gelation using thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), water contact angle measurement, and cross-linking test, respectively. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:155 / 164
页数:10
相关论文
共 77 条
[1]   ROMP from ROMP: A New Approach to Graft Copolymer Synthesis [J].
Allen, Matthew J. ;
Wangkanont, Kittikhun ;
Raines, Ronald T. ;
Kiessling, Laura L. .
MACROMOLECULES, 2009, 42 (12) :4023-4027
[2]   A Dynamic Duo: Pairing Click Chemistry and Postpolymerization Modification To Design Complex Surfaces [J].
Arnold, Rachelle M. ;
Patton, Derek L. ;
Popik, Vladimir V. ;
Locklin, Jason .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) :2999-3008
[3]   Clickable Poly(ethylene glycol)-Based Copolymers Using Azide-Alkyne Click Cycloaddition-Mediated Step-Growth Polymerization [J].
Arslan, Mehmet ;
Gok, Ozgul ;
Sanyal, Rana ;
Sanyal, Amitav .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2014, 215 (22) :2237-2247
[4]   "Clicking" Polymers or Just Efficient Linking: What Is the Difference? [J].
Barner-Kowollik, Christopher ;
Du Prez, Filip E. ;
Espeel, Pieter ;
Hawker, Craig J. ;
Junkers, Tanja ;
Schlaad, Helmut ;
Van Camp, Wim .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) :60-62
[5]   Click Chemistry beyond Metal-Catalyzed Cycloaddition [J].
Becer, C. Remzi ;
Hoogenboom, Richard ;
Schubert, Ulrich S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (27) :4900-4908
[6]   Living ring-opening metathesis polymerization [J].
Bielawski, Christopher W. ;
Grubbs, Robert H. .
PROGRESS IN POLYMER SCIENCE, 2007, 32 (01) :1-29
[7]   Synthesis of end-functionalized poly(norbornene)s via ring-opening metathesis polymerization [J].
Bielawski, CW ;
Benitez, D ;
Morita, T ;
Grubbs, RH .
MACROMOLECULES, 2001, 34 (25) :8610-8618
[8]   Metal-Free Functionalization of Linear Polyurethanes by Thiol-Maleimide Coupling Reactions [J].
Billiet, Leen ;
Gok, Ozgul ;
Dove, Andrew P. ;
Sanyal, Amitav ;
Nguyen, Le-Thu T. ;
Du Prez, Filip E. .
MACROMOLECULES, 2011, 44 (20) :7874-7878
[9]   'Click' chemistry in polymer and materials science [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54
[10]   Development of thermal and photochemical strategies for thiol-ene click polymer functionalization [J].
Campos, Luis M. ;
Killops, Kato L. ;
Sakai, Ryosuke ;
Paulusse, Jos M. J. ;
Damiron, Denis ;
Drockenmuller, Eric ;
Messmore, Benjamin W. ;
Hawker, Craig J. .
MACROMOLECULES, 2008, 41 (19) :7063-7070