Indeno[2,1-a]fluorene: An Air-Stable ortho-Quinodimethane Derivative

被引:207
作者
Shimizu, Akihiro [1 ]
Tobe, Yoshito [1 ]
机构
[1] Osaka Univ, Div Frontier Mat Sci, Grad Sch Engn Sci, Toyonaka, Osaka 5608531, Japan
关键词
acenes; antiaromaticity; polycycles; quinodimethanes; radicals; HYDROCARBURES INDENOFLUORENIQUES ORTHOQUINOIDES; PROTON-RESONANCE SPECTROSCOPY; UNSATURATED RING-SYSTEMS; PI-ELECTRONIC STRUCTURE; PHOTOCHEMICAL PREPARATION; PI; PI-BIRADICALOID HYDROCARBONS; AROMATIC-HYDROCARBON; BIRADICAL CHARACTER; KEKULE STRUCTURES; BENZENE NUCLEUS;
D O I
10.1002/anie.201101950
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new isomer: 11,12-Dimesitylindeno[2,1-a]fluorene was synthesized and isolated in crystal form. The indenofluorene exhibits significant bond-length alternation in the o-quinodimethane structure, limited singlet biradical character, and weakly antiaromatic character. Optical and electrochemical properties suggest that indeno[2,1-a]fluorene derivatives may be candidates for optoelectronic materials. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6906 / 6910
页数:5
相关论文
共 78 条
[1]  
[Anonymous], 2000, Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives
[2]  
[Anonymous], ANGEW CHEM
[3]  
Anthony J. E., 2008, ANGEW CHEM, V120, P460
[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]   NEUTRAL AND CHARGED BIRADICALS, ZWITTERIONS, FUNNELS IN S1, AND PROTON TRANSLOCATION - THEIR ROLE IN PHOTOCHEMISTRY, PHOTOPHYSICS, AND VISION [J].
BONACICKOUTECKY, V ;
KOUTECKY, J ;
MICHL, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1987, 26 (03) :170-189
[7]   CYCLOPENT[A]INDENE (BENZOPENTALENE) - GENERATION BY FLASH VACUUM PYROLYSIS AND SUBSEQUENT DIMERIZATION [J].
BROWN, RFC ;
CHOI, N ;
COULSTON, KJ ;
EASTWOOD, FW ;
WIERSUM, UE ;
JENNESKENS, LW .
TETRAHEDRON LETTERS, 1994, 35 (25) :4405-4408
[8]  
CHALVET O, 1956, B SOC CHIM FR, P1667
[9]   Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes [J].
Chase, Daniel T. ;
Rose, Bradley D. ;
McClintock, Sean P. ;
Zakharov, Lev N. ;
Haley, Michael M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1127-1130
[10]   The simple principle of decomposition of aromatic hydrogen carbons and their absorption spectra (Aromatic hydrogen carbons, 20. Announcement). [J].
Clar, E .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1936, 69 :607-614