Poly(thiolactone) homo- and copolymers from maleimide thiolactone: synthesis and functionalization

被引：29
作者：
Rudolph, Tobias [1 ,2 ]
Espeel, Pieter [3 ]
Du Prez, Filip E. [3 ]
Schacher, Felix H. [1 ,2 ]
机构：
[1] Univ Jena, Lab Organ & Macromol Chem, D-07743 Jena, Germany
[2] Univ Jena, Jena Ctr Soft Matter, D-07743 Jena, Germany
[3] Univ Ghent, Dept Organ & Macromol Chem, Polymer Chem Res Grp, B-9000 Ghent, Belgium
来源：
POLYMER CHEMISTRY | 2015年 / 6卷 / 23期
关键词：
MICHAEL ADDITION-REACTIONS; N-SUBSTITUTED MALEIMIDES; ONE-POT; RADICAL COPOLYMERIZATION; CONTAINING POLYMERS; CLICK CHEMISTRY; POLYMERIZATION; AMINE; ISOPROPYLACRYLAMIDE; STYRENE;
D O I：
10.1039/c5py00329f
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
We describe the synthesis of a thiolactone-functionalized maleimide (MITla), and its (co)polymerization into poly(thiolactone) homo- and copolymers via controlled or free radical polymerization (CRP or FRP) techniques. Homopolymers were synthesized using FRP whereas MITla was copolymerized with styrene and N-iso-propylacrylamide (NIPAAm) via RAFT. In that way, we were able to combine the properties of a maleimide with the possibility to use the thiolactone side chain functionality in subsequent double modification reactions. Thiolactones are susceptible to nucleophilic ring-opening in the presence of primary amines, releasing a thiol moiety that can be used for conjugate addition (nucleophilic thiol-ene) reactions afterwards. We synthesized and characterized copolymers of different compositions, followed by site-specific double modification reactions with a combination of n-butylamine and methyl acrylate.
引用
收藏
页码：4240 / 4251
页数：12
相关论文
共 57 条
[1]   New methods of polymer synthesis [J].
Barner-Kowollik, Christopher ;
Lutz, Jean-Francois ;
Perrier, Sebastien .
POLYMER CHEMISTRY, 2012, 3 (07) :1677-1679
[2]   "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
[3]   Block copolymers - Designer soft materials [J].
Bates, FS ;
Fredrickson, GH .
PHYSICS TODAY, 1999, 52 (02) :32-38
[4]   Polythiolactone-Based Redox-Responsive Layers for the Reversible Release of Functional Molecules [J].
Belbekhouche, Sabrina ;
Reinicke, Stefan ;
Espeel, Pieter ;
Du Prez, Filip E. ;
Eloy, Pierre ;
Dupont-Gillain, Christine ;
Jonas, Alain M. ;
Demoustier-Champagne, Sophie ;
Glinel, Karine .
ACS APPLIED MATERIALS & INTERFACES, 2014, 6 (24) :22457-22466
[5]   'Click' chemistry in polymer and materials science [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54
[6]   Control of Glycopolymer Nanoparticle Morphology by a One-Pot, Double Modification Procedure Using Thiolactones [J].
Chen, Yong ;
Espeel, Pieter ;
Reinicke, Stefan ;
Du Prez, Filip E. ;
Stenzel, Martina H. .
MACROMOLECULAR RAPID COMMUNICATIONS, 2014, 35 (12) :1128-1134
[7]   The synthesis of poly(MA-alt-NIPA) copolymer, spectroscopic characterization, and the investigation of solubility profile-viscosity behavior [J].
Demircan, D. ;
Kibarer, G. ;
Guner, A. ;
Rzaev, Z. M. O. ;
Ersoy, E. .
CARBOHYDRATE POLYMERS, 2008, 72 (04) :682-694
[8]   Radical copolymerization of N-isopropylacrylamide with anhydrides of maleic and citraconic acids [J].
Dinçer, S ;
Köseli, V ;
Kesim, H ;
Rzaev, ZMO ;
Piskin, E .
EUROPEAN POLYMER JOURNAL, 2002, 38 (11) :2143-2152
[9]   "Click"-Inspired Chemistry in Macromolecular Science: Matching Recent Progress and User Expectations [J].
Espeel, Pieter ;
Du Prez, Filip E. .
MACROMOLECULES, 2015, 48 (01) :2-14
[10]   One-pot multi-step reactions based on thiolactone chemistry: A powerful synthetic tool in polymer science [J].
Espeel, Pieter ;
Du Prez, Filip E. .
EUROPEAN POLYMER JOURNAL, 2015, 62 :247-272
123456