Self-condensation-type direct arylation synthesis of naphthalene bisimide-bithiophene alternating copolymers

被引:0
作者
Kazuhiro Nakabayashi
Haruka Fukuzawa
Masaya Yamada
Hideharu Mori
机构
[1] Yamagata University,Graduate School of Organic Materials Science
来源
Microsystem Technologies | 2017年 / 23卷
关键词
DMAc; Intramolecular Charge Transfer; Phosphine Ligand; Thermal Gravimetric; PCy3;
D O I
暂无
中图分类号
学科分类号
摘要
The self-condensation-type direct arylation of naphthalene bisimide (NBI)-bithiophene alternating copolymers (PNBI2T), which was classified as one of high-performance acceptor polymers in organic field-effect transistors and organic photovoltaics, was developed. A new AB-type NBI monomer (NBI2T-Br) was designed for the self-condensation-type direct arylation. A PNBI2T was successfully synthesized by using NBI2T-Br; as a result of screening of the reaction conditions, the PNBI2T with Mn = 13,000 was obtained in the high yield (87 %) in the presence of Pd(OAc)2, PCy3·HBF4, PivOH, and K2CO3. Furthermore, analyses of spectroscopy, optical, electrochemical, and thermal properties indicated that the PNBI2T with the desired structure was synthesized by the self-condensation-type direct arylation.
引用
收藏
页码:3817 / 3823
页数:6
相关论文
共 83 条
[1]  
Bao Z(1995)Exploration of the stille coupling reaction for the synthesis of functional polymers J Am Chem Soc 117 12426-12435
[2]  
Chan WK(2012)Low-cost synthesis and physical characterization of thieno[3,4- J Org Chem 77 8167-8173
[3]  
Yu L(2013)]pyrrole-4,6-dione-based polymers Adv Mater 25 6642-6671
[4]  
Berrouard P(2010)25th anniversary article: a decade of organic/polymeric photovoltaic research Adv Mater 22 4427-4447
[5]  
Dufresne S(2010)Functional organic field-effect transistors Adv Mater 22 478-482
[6]  
Pron A(2013)High-mobility ambipolar transistors and high-gain inverters from a donor-acceptor copolymer semiconductor Adv Funct Mater 13 5719-5727
[7]  
Veilleux J(2013)High-mobility air-stable naphthalene diimide-based copolymer containing extended π-conjugation for n-channel organic field effect transistors Prog Polym Sci 38 1805-1814
[8]  
Leclerc M(2015)Direct arylation polycondensation as simplified alternative for the synthesis of conjugated (co)polymers Macromol Rapid Commun 36 1061-1068
[9]  
Dou L(2014)Scope and limitations of a direct arylation polycondensation scheme in the synthesis of PCPDTBT-type copolymers ACS Macro Lett 3 819-823
[10]  
You J(2015)Identifying homocouplings as critical side reactions in direct arylation polycondensation J Am Chem Soc 137 6705-6711