Boron Subphthalocyanine Polymers by Facile Coupling to Poly(acrylic acid-ran-styrene) Copolymers Synthesized by Nitroxide-Mediated Polymerization and the Associated Problems with Autoinitiation

被引：17

作者：

Lessard, Benoit H. ^{[1
]}

Bender, Timothy P. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem Engn & Appl Chem, Toronto, ON M5S3E5, Canada

来源：

MACROMOLECULAR RAPID COMMUNICATIONS | 2013年 / 34卷 / 07期

基金：

加拿大自然科学与工程研究理事会;

关键词：

acrylic acid; autoinitiation; boron; carboxylic; functionalization; nitroxide-mediated polymerization; polyphthalocyanines; polystyrene; suphthalocyanine; FREE-RADICAL POLYMERIZATION; OPEN-CIRCUIT VOLTAGE; BUTYL ACRYLATE; KINETICS; STYRENE;

D O I：

10.1002/marc.201200787

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Boron subphthalocyanines (BsubPcs) are macrocyclic aromatic small molecules containing a chelated boron atom. BsubPcs have interesting optoelectronic and physical properties, justifying their use in various organic electronic devices such as organic solar cells and organic light-emitting diodes. However, our group has only recently reported the first incorporation of a BsubPc moiety into a polymer using a two-step post-polymerization procedure. This communication outlines the use of acrylic acid as a method for obtaining carboxylic acid functional copolymers for the facile coupling to BsubPc post polymerization. In addition, the observations and the proposed mechanism of a side product unique to the copolymerization of acrylic acid and styrene due to autoinitiation are presented.

引用

页码：568 / 573

页数：6

共 32 条

[1] Boron Subphthalocyanine Chloride as an Electron Acceptor for High-Voltage Fullerene-Free Organic Photovoltaics [J].

Beaumont, Nicola ;

Cho, Sang Wan ;

Sullivan, Paul ;

Newby, David ;

Smith, Kevin E. ;

Jones, Tim S. .

ADVANCED FUNCTIONAL MATERIALS, 2012, 22 (03) :561-566

[2] Optimization of the nitroxide-mediated radical polymerization conditions for styrene and tert-butyl acrylate in an automated parallel synthesizer [J].

Becer, C. Remzi ;

Paulus, Renzo M. ;

Hoogenboom, Richard ;

Schubert, Ulrich S. .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (21) :6202-6213

[3] Organic photovoltaics: technology and market [J].

Brabec, CJ .

SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2004, 83 (2-3) :273-292

[4] Polymer solar cells: Recent development and possible routes for improvement in the performance [J].

Cai, Wanzhu ;

Gong, Xiong ;

Cao, Yong .

SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2010, 94 (02) :114-127

[5] First nitroxide-mediated controlled free-radical polymerization of acrylic acid [J].

Couvreur, L ;

Lefay, C ;

Belleney, J ;

Charleux, B ;

Guerret, O ;

Magnet, S .

MACROMOLECULES, 2003, 36 (22) :8260-8267

[6] A Boron Subphthalocyanine Polymer: Poly(4-methylstyrene)-co-poly(phenoxy boron subphthalocyanine) [J].

Dang, Jeremy D. ;

Virdo, Jessica D. ;

Lessard, Benoit H. ;

Bultz, Elijah ;

Paton, Andrew S. ;

Bender, Timothy P. .

MACROMOLECULES, 2012, 45 (19) :7791-7798

[7] Subphthalocyanines as narrow band red-light emitting materials [J].

Diaz, David D. ;

Bolink, Henk J. ;

Cappelli, Luca ;

Claessens, Christian G. ;

Coronado, Eugenio ;

Torres, Tomas .

TETRAHEDRON LETTERS, 2007, 48 (27) :4657-4660

[8] Mechanisms and kinetics of nitroxide-controlled free radical polymerization [J].

Fukuda, T ;

Terauchi, T ;

Goto, A ;

Ohno, K ;

Tsujii, Y ;

Miyamoto, T ;

Kobatake, S ;

Yamada, B .

MACROMOLECULES, 1996, 29 (20) :6393-6398

[9] NARROW MOLECULAR-WEIGHT RESINS BY A FREE-RADICAL POLYMERIZATION PROCESS [J].

GEORGES, MK ;

VEREGIN, RPN ;

KAZMAIER, PM ;

HAMER, GK .

MACROMOLECULES, 1993, 26 (11) :2987-2988

[10] Nitroxide-Mediated Radical Polymerization: Limitations and Versatility [J].

Grubbs, Robert B. .

POLYMER REVIEWS, 2011, 51 (02) :104-137

← 1 2 3 4 →