The Marriage of Metallacycle Transfer Chemistry with Suzuki-Miyaura Cross-Coupling To Give Main Group Element-Containing Conjugated Polymers

被引:110
作者
He, Gang [1 ]
Kang, Le [1 ]
Delgado, William Torres [1 ]
Shynkaruk, Olena [1 ]
Ferguson, Michael J. [1 ]
McDonald, Robert [1 ]
Rivard, Eric [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
ZIRCONOCENE DICHLORIDE; PHASE-SEPARATION; SOLAR-CELLS; ROUTE; SELENOPHENE; ZIRCONIUM; POLYTELLUROPHENES; HETEROCYCLES; OLIGOMERS; VERSATILE;
D O I
10.1021/ja402242z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A versatile and general synthetic route for the synthesis of conjugated main group element-based polymers, previously inaccessible by conventional means, is reported. These polymers contain five-membered chalcogenophene rings based on S, Se, and Te, and we demonstrate that optoelectronic properties can be readily tuned via controlled atom substitution chemistry. In addition, regioregular hybrid thiophene selenophene tellurophene and selenophene fluorene copolymers were synthesized to provide a further illustration of the scope of the presented metallacycle transfer/cross-coupling polymerization method.
引用
收藏
页码:5360 / 5363
页数:4
相关论文
共 53 条
[1]   Electroluminescent polymers [J].
Akcelrud, L .
PROGRESS IN POLYMER SCIENCE, 2003, 28 (06) :875-962
[2]   Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications [J].
Beaujuge, Pierre M. ;
Frechet, Jean M. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) :20009-20029
[3]   Development of Novel Conjugated Donor Polymers for High-Efficiency Bulk-Heterojunction Photovoltaic Devices [J].
Chen, Junwu ;
Cao, Yong .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (11) :1709-1718
[4]   Polymers for flexible displays: From material selection to device applications [J].
Choi, Myeon-Cheon ;
Kim, Youngkyoo ;
Ha, Chang-Sik .
PROGRESS IN POLYMER SCIENCE, 2008, 33 (06) :581-630
[5]   Bulk Heterojunction Solar Cells Using Thieno[3,4-c]pyrrole-4,6-dione and Dithieno[3,2-b:2′,3′-d]silole Copolymer with a Power Conversion Efficiency of 7.3% [J].
Chu, Ta-Ya ;
Lu, Jianping ;
Beaupre, Serge ;
Zhang, Yanguang ;
Pouliot, Jean-Remi ;
Wakim, Salem ;
Zhou, Jiayun ;
Leclerc, Mario ;
Li, Zhao ;
Ding, Jianfu ;
Tao, Ye .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4250-4253
[6]   Poly(cyclopenta[c]selenophene): a new polyselenophene [J].
Das, Soumyajit ;
Zade, Sanjio S. .
CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1168-1170
[7]   Nature of the species present in the zirconocene dichloride butyllithium reaction mixture [J].
Dioumaev, VK ;
Harrod, JF .
ORGANOMETALLICS, 1997, 16 (07) :1452-1464
[8]   Lewis Base Sequestered Chalcogen Dihalides: Synthetic Sources of ChX2 (Ch = Se, Te; X = Cl, Br) [J].
Dutton, Jason L. ;
Farrar, Gregory J. ;
Sgro, Michael J. ;
Battista, Taylor L. ;
Ragogna, Paul J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) :10263-10271
[9]   THE ELECTRONIC AND ELECTROCHEMICAL PROPERTIES OF POLY(PHENYLENE VINYLENES) AND POLY(THIENYLENE VINYLENES) - AN EXPERIMENTAL AND THEORETICAL-STUDY [J].
ECKHARDT, H ;
SHACKLETTE, LW ;
JEN, KY ;
ELSENBAUMER, RL .
JOURNAL OF CHEMICAL PHYSICS, 1989, 91 (02) :1303-1315
[10]   METALLACYCLE TRANSFER FROM ZIRCONIUM TO MAIN-GROUP ELEMENTS - A VERSATILE SYNTHESIS OF HETEROCYCLES [J].
FAGAN, PJ ;
NUGENT, WA ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :1880-1889