Phosphonium- and borate-bridged zwitterionic ladder stilbene and its extended analogues

被引:177
作者
Fukazawa, Aiko [1 ,2 ]
Yamada, Hiroshi [1 ,2 ]
Yamaguchi, Shigehiro [1 ,2 ]
机构
[1] Nagoya Univ, Grad Sch Sci, Nagoya, Aichi 4648602, Japan
[2] Japan Sci & Technol Agcy, SORST, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
boron; fluorescence; phosphorus; pi conjugation; zwitterions;
D O I
10.1002/anie.200801834
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A rung up: A polar and rigid stilbene with phosphonium and borate bridging moieties was synthesized by the spontaneous cyclization of a boryl- and phosphanyl-substituted diphenylacetylene (see picture). Various extended ladder π-conjugated molecules can be synthesized in this manner. The zwitterionic moiety significantly modulates the electronic structure, thus leading to attractive fluorescence and redox properties. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5582 / 5585
页数:4
相关论文
共 49 条
[1]   Electronic and optical properties of ladder-type heteraborins [J].
Agou, Tomohiro ;
Kobayashi, Junji ;
Kawashima, Takayuki .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) :8051-8060
[2]   Development of a general route to periphery-functionalized azaborines and ladder-type azaborines by using common intermediates [J].
Agou, Tomohiro ;
Kobayashi, Junji ;
Kawashima, Takayuki .
CHEMICAL COMMUNICATIONS, 2007, (30) :3204-3206
[3]   Syntheses, structure, and optical properties of ladder-type fused azaborines [J].
Agou, Tomohiro ;
Kobayashi, Junji ;
Kawashima, Takayuki .
ORGANIC LETTERS, 2006, 8 (11) :2241-2244
[4]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[5]   Functionalized acenes and heteroacenes for organic electronics [J].
Anthony, John E. .
CHEMICAL REVIEWS, 2006, 106 (12) :5028-5048
[6]   From model compounds to extended π-conjugated systems:: Synthesis and properties of dithieno[3,2-b:2′,3′-d]phospholes [J].
Baumgartner, T ;
Bergmans, W ;
Kárpáti, T ;
Neumann, T ;
Nieger, M ;
Nyulászi, L .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (16) :4687-4699
[7]   The dithieno[3,2-b:2′,3′-d]phosphole system:: A novel building block for highly luminescent π-conjugated materials [J].
Baumgartner, T ;
Neumann, T ;
Wirges, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6197-6201
[8]  
Baumgartner T., 2004, ANGEW CHEM, V116, P6323
[9]   Organophosphorus π-conjugated materials [J].
Baumgartner, Thomas ;
Reau, Regis .
CHEMICAL REVIEWS, 2006, 106 (11) :4681-4727
[10]   PHOSPHONIOBORATOACETYLENES - C2 STABILIZED BY DONOR AND ACCEPTOR MOLECULES [J].
BESTMANN, HJ ;
BEHL, H ;
BREMER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09) :1219-1221