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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 30期
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
[21]   PHOTOCHEMICAL PREPARATION OF ORTHO-XYLYLENE FROM 1,4-DIHYDROPHTHALAZINE IN RIGID GLASS [J].
FLYNN, CR ;
MICHL, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (17) :5802-5803
[22]   An isolable o-quinodimethane and its fixation of molecular oxygen to give an endoperoxide [J].
Ghereg, Dumitru ;
El Kettani, Sakina Ech-Cherif ;
Lazraq, Mohamed ;
Ranaivonjatovo, Henri ;
Schoeller, Wolfgang W. ;
Escudie, Jean ;
Gornitzka, Heinz .
CHEMICAL COMMUNICATIONS, 2009, (32) :4821-4823
[23]  
GUNTHER H, 1978, LIEBIGS ANN CHEM, P150
[24]   First stable 7,7,8,8-tetraaryl-o-quinodimethane:: isolation, X-ray structure, electrochromic response of 9,10-bis(dianisylmethylene)-9,10-dihydrophenanthrene [J].
Iwashita, S ;
Ohta, E ;
Higuchi, H ;
Kawai, H ;
Fujiwara, K ;
Ono, K ;
Takanaka, M ;
Suzuki, T .
CHEMICAL COMMUNICATIONS, 2004, (18) :2076-2077
[25]   How diradicaloid is a stable diradical? [J].
Jung, YS ;
Head-Gordon, M .
CHEMPHYSCHEM, 2003, 4 (05) :522-525
[26]  
Kamada K., 2007, Angew. Chem. Int. Ed. Engl, V119, P3614
[27]   Strong two-photon absorption of singlet diradical hydrocarbons [J].
Kamada, Kenji ;
Ohta, Koji ;
Kubo, Takashi ;
Shimizu, Akihiro ;
Morita, Yasushi ;
Nakasuji, Kazuhiro ;
Kishi, Ryohei ;
Ohta, Suguru ;
Furukawa, Shin-ichi ;
Takahashi, Hideaki ;
Nakano, Masayoshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3544-3546
[28]   Singlet Diradical Character from Experiment [J].
Kamada, Kenji ;
Ohta, Koji ;
Shimizu, Akihiro ;
Kubo, Takashi ;
Kishi, Ryohei ;
Takahashi, Hideaki ;
Botek, Edith ;
Champagne, Benoit ;
Nakano, Masayoshi .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2010, 1 (06) :937-940
[29]  
Kawase T., 2010, Angew. Chem, V122, P7894
[30]   Dinaphthopentalenes: Pentalene Derivatives for Organic Thin-Film Transistors [J].
Kawase, Takeshi ;
Fujiwara, Takeru ;
Kitamura, Chitoshi ;
Konishi, Akihito ;
Hirao, Yasukazu ;
Matsumoto, Kouzou ;
Kurata, Hiroyuki ;
Kubo, Takashi ;
Shinamura, Shoji ;
Mori, Hiroki ;
Miyazaki, Eigo ;
Takimiya, Kazuo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (42) :7728-7732
12345678