Synthesis of poly(3-hexylthiophene) based rod-coil conjugated block copolymers via photoinduced metal-free atom transfer radical polymerization

被引:24
作者
Tam Huu Nguyen [1 ]
Nguyen, Le-Thu T. [1 ]
Viet Quoc Nguyen [2 ]
Lan Ngoc Tan Phan [1 ]
Zhang, Geng [3 ]
Yokozawa, Tsutomu [3 ]
Dung Thuy Thi Phung [1 ]
Ha Tran Nguyen [1 ,4 ]
机构
[1] Vietnam Natl Univ Ho Chi Minh City VNU HCM, Fac Mat Technol, Univ Technol, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
[2] VNU HCM, Natl Key Lab Polymer & Composite Mat, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
[3] Kanagawa Univ Rokkakubashi, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan
[4] VNU HCM, Mat Technol Key Lab Mtlab, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
关键词
REGIOREGULAR POLY(3-HEXYLTHIOPHENE); DIBLOCK COPOLYMERS; FACILE SYNTHESIS; ORGANIC PHOTOVOLTAICS; PERFORMANCE; METHACRYLATE); POLYTHIOPHENE; DRIVEN; MORPHOLOGY; MECHANISM;
D O I
10.1039/c8py00361k
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The photo-mediated metal-free atom transfer radical polymerization approach has been investigated for the first time to polymerize methyl methacrylate, N,N-dimethylamino-2-ethyl methacrylate, 2-([4,6-dichlorotriazin-2-yl]oxy)ethyl methacrylate and a mixture of methyl methacrylate and 1-pyrenemethyl methacrylate from a regioregular poly(3-hexylthiophene) (P3HT) macroinitiator to produce well-defined rod-coil conjugated diblock copolymers, highly relevant for use as organic electronic materials without metal catalyst contamination. This was achieved using pyrene and a pyrenyl N-substituted phenothiazine (PPTh) as UV light photoredox catalysts. Spectral and chromatographic results revealed that the applied synthetic approach generated P3HT-based diblock copolymers in a controlled manner and with narrow molecular weight distributions (D <= 1.3). From a comparison of the efficiency of the photocatalysts, PPTh has shown advantages over pyrene, including much lower catalyst content and higher polymerization conversions.
引用
收藏
页码:2484 / 2493
页数:10
相关论文
共 65 条
[1]   Amphiphilic Block Copolymers Containing Regioregular Poly(3-hexylthiophene) and Poly(2-ethyl-2-oxazoline) [J].
Alemseghed, Mussie G. ;
Servello, John ;
Hundt, Nadia ;
Sista, Prakash ;
Biewer, Michael C. ;
Stefan, Mihaela C. .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2010, 211 (12) :1291-1297
[2]   Conventional Type II photoinitiators as activators for photoinduced metal-free atom transfer radical polymerization [J].
Allushi, Andrit ;
Kutahya, Ceren ;
Aydogan, Cansu ;
Kreutzer, Johannes ;
Yilmaz, Gorkem ;
Yagci, Yusuf .
POLYMER CHEMISTRY, 2017, 8 (12) :1972-1977
[3]   Photoinitiated Metal-Free Controlled/Living Radical Polymerization Using Polynuclear Aromatic Hydrocarbons [J].
Allushi, Andrit ;
Jockusch, Steffen ;
Yilmaz, Gorkem ;
Yagci, Yusuf .
MACROMOLECULES, 2016, 49 (20) :7785-7792
[4]   THERMOREVERSIBLE GELATION OF SOLUTIONS OF SYNDIOTACTIC POLY(METHYL METHACRYLATE) IN TOLUENE - A 2-STEP MECHANISM [J].
BERGHMANS, M ;
THIJS, S ;
CORNETTE, M ;
BERGHMANS, H ;
DESCHRYVER, FC ;
MOLDENAERS, P ;
MEWIS, J .
MACROMOLECULES, 1994, 27 (26) :7669-7676
[5]   Nanoporous poly(3-alkylthiophene) thin films generated from block copolymer templates [J].
Boudouris, Bryan W. ;
Frisbie, C. Daniel ;
Hillmyer, Marc A. .
MACROMOLECULES, 2008, 41 (01) :67-75
[6]   Cooperative Assembly of Pyrene-Functionalized Donor/Acceptor Blend for Ordered Nanomorphology by Intermolecular Noncovalent π-π Interactions [J].
Chen, Lie ;
Peng, Siwan ;
Chen, Yiwang .
ACS APPLIED MATERIALS & INTERFACES, 2014, 6 (11) :8115-8123
[7]   Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization [J].
Dadashi-Silab, Sajjad ;
Pan, Xiangcheng ;
Matyjaszewski, Krzysztof .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (25) :5972-5977
[8]   Facile synthesis of well-defined block copolymers containing regioregular poly(3-hexyl thiophene) via anionic macroinitiation method and their self-assembly behavior [J].
Dai, Chi-An ;
Yen, Wei-Che ;
Lee, Yi-Huan ;
Ho, Chun-Chi ;
Su, Wei-Fang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :11036-+
[9]   Facile synthesis of poly(3-hexylthiophene)-block-poly(ethylene oxide) copolymers via Steglich esterification [J].
Erothu, Harikrishna ;
Sohdi, Arun A. ;
Kumar, Anitha C. ;
Sutherland, Andrew J. ;
Dagron-Lartigau, Christine ;
Allal, Ahmed ;
Hiorns, Roger C. ;
Topham, Paul D. .
POLYMER CHEMISTRY, 2013, 4 (13) :3652-3655
[10]   Probing Side Chain Dynamics of Branched Macromolecules by Pyrene Excimer Fluorescence [J].
Farhangi, Shiva ;
Duhamel, Jean .
MACROMOLECULES, 2016, 49 (01) :353-361