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
    Agou, Tomohiro
    Kobayashi, Junji
    Kawashima, Takayuki
    [J]. 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
    Agou, Tomohiro
    Kobayashi, Junji
    Kawashima, Takayuki
    [J]. CHEMICAL COMMUNICATIONS, 2007, (30) : 3204 - 3206
  • [3] Syntheses, structure, and optical properties of ladder-type fused azaborines
    Agou, Tomohiro
    Kobayashi, Junji
    Kawashima, Takayuki
    [J]. ORGANIC LETTERS, 2006, 8 (11) : 2241 - 2244
  • [4] The larger acenes: Versatile organic semiconductors
    Anthony, John E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 452 - 483
  • [5] Functionalized acenes and heteroacenes for organic electronics
    Anthony, John E.
    [J]. 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
    Baumgartner, T
    Bergmans, W
    Kárpáti, T
    Neumann, T
    Nieger, M
    Nyulászi, L
    [J]. 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
    Baumgartner, T
    Neumann, T
    Wirges, B
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6197 - 6201
  • [8] Baumgartner T., 2004, ANGEW CHEM, V116, P6323
  • [9] Organophosphorus π-conjugated materials
    Baumgartner, Thomas
    Reau, Regis
    [J]. CHEMICAL REVIEWS, 2006, 106 (11) : 4681 - 4727
  • [10] PHOSPHONIOBORATOACETYLENES - C2 STABILIZED BY DONOR AND ACCEPTOR MOLECULES
    BESTMANN, HJ
    BEHL, H
    BREMER, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09): : 1219 - 1221