Borylated Dibenzoborepin: Synthesis by Skeletal Rearrangement and Photochromism Based on Bora-Nazarov Cyclization

被引：87
作者：
Iida, Azusa [1 ,2 ,3 ]
Saito, Shohei [1 ,2 ,3 ]
Sasamori, Takahiro [4 ]
Yamaguchi, Shigehiro [1 ,2 ,3 ]
机构：
[1] Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] CREST Japan Sci & Technol Agcy JST, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[4] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 13期
关键词：
boron; cyclization; electrocyclic reactions; photochromism; structure elucidation; 3-COORDINATE ORGANOBORON COMPOUNDS; AMORPHOUS MOLECULAR MATERIALS; NONLINEAR-OPTICAL PROPERTIES; PI-ELECTRON MATERIALS; TRIVALENT BORON; ELECTROLUMINESCENT DEVICES; SINGLE-PHOTON; PHOTOCHEMISTRY; ACCEPTOR; POLYMERS;
D O I：
10.1002/anie.201210236
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
It's a boron kind of magic: A complex reaction sequence involving a skeletal rearrangement leads to 10-dimesitylboryl-substituted dibenzoborepin in a one-pot transformation in good yield. The borylborepin shows remarkable photochromic properties and undergoes a bora-Nazarov cyclization to give a deep-blue compound with an allyl cation-like C-B-C substructure. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：3760 / 3764
页数：5
相关论文
共 64 条
  • [1] The Pentaphenylborole-2,6-Lutidine Adduct: A System with Unusual Thermochromic and Photochromic Properties
    Ansorg, Kay
    Braunschweig, Holger
    Chiu, Ching-Wen
    Engels, Bernd
    Gamon, Daniela
    Huegel, Markus
    Kupfer, Thomas
    Radacki, Krzysztof
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) : 2833 - 2836
  • [2] Araneda JF, 2012, ANGEW CHEM, V124, P8674
  • [3] Photochemical Synthesis of a Ladder Diborole: A New Boron-Containing Conjugate Material
    Araneda, Juan F.
    Neue, Benedikt
    Piers, Warren E.
    Parvez, Masood
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (34) : 8546 - 8550
  • [4] CONFORMATIONAL-ANALYSIS OF TRIARYLBORANES
    BLOUNT, JF
    FINOCCHIARO, P
    GUST, D
    MISLOW, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (21) : 7019 - 7029
  • [5] ALKYLALKYLIDENEBORANES R-B=C(SIME3)2 - ISOLABLE MOLECULES WITH A 2-COORDINATED SEXTET BORON ATOM
    BOESE, R
    PAETZOLD, P
    TAPPER, A
    ZIEMBINSKI, R
    [J]. CHEMISCHE BERICHTE, 1989, 122 (06) : 1057 - 1060
  • [6] Caruso A., 2010, Angewandte Chemie, V122, P4309
  • [7] Synthesis of Functionalizable Boron-Containing π-Electron Materials that Incorporate Formally Aromatic Fused Borepin Rings
    Caruso, Anthony, Jr.
    Siegler, Maxime A.
    Tovar, John D.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (25) : 4213 - 4217
  • [8] A NEW ZWITTERIONIC SALT FOR NONLINEAR OPTICS - (4'-[METHYL(DIPHENYL)PHOSPHONIO]BIPHENYL-4-YL)TRIPHENYLBORATE
    CHING, KC
    LEQUAN, M
    LEQUAN, RM
    GRISARD, A
    MARKOVITSI, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1991, 87 (14): : 2225 - 2228
  • [9] THERMAL GENERATION AND TRANSFORMATION OF THE BOREPIN RING-SYSTEM - A PARADIGM OF PERICYCLIC PROCESSES
    EISCH, JJ
    GALLE, JE
    SHAFII, B
    RHEINGOLD, AL
    [J]. ORGANOMETALLICS, 1990, 9 (08) : 2342 - 2349
  • [10] SYNTHESIS OF HEPTAPHENYLBOREPIN VIA THERMAL REARRANGEMENT OF HEPTAPHENYL-7-BORABICYCLO[2.2.1]HEPTADIENE
    EISCH, JJ
    GALLE, JE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (15) : 4436 - 4437
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