A Stable Non-Kekule Singlet Biradicaloid from meso-Free 5,10,20,25-Tetrakis(Pentafluorophenyl)-Substituted [26]Hexaphyrin(1.1.1.1.1.1)

被引:77
作者
Koide, Taro [2 ]
Furukawa, Ko [3 ]
Shinokubo, Hiroshi [1 ]
Shin, Jae-Yoon [4 ,5 ]
Kim, Kil Suk [4 ,5 ]
Kim, Dongho [4 ,5 ]
Osuka, Atsuhiro [2 ]
机构
[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[3] Natl Inst Nat Sci, Inst Mol Sci, Okazaki, Aichi 4448585, Japan
[4] Yonsei Univ, Spect Lab Funct Elect Syst, Seoul 120749, South Korea
[5] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
基金
新加坡国家研究基金会;
关键词
ABSORPTION; DIMERS;
D O I
10.1021/ja101040s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A meso,meso-diketohexaphyrin was isolated and characterized as a chemically stable non-Kekule singlet biradicaloid. Two unpaired electrons are seemingly delocalized on two tripyrrolic units separated by C=O bonds. These results underscore the potential of expanded porphyrins to achieve unique electronic states.
引用
收藏
页码:7246 / +
页数:4
相关论文
共 20 条
[1]   ANOMALOUS PARAMAGNETISM OF COPPER ACETATE [J].
BLEANEY, B ;
BOWERS, KD .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL AND PHYSICAL SCIENCES, 1952, 214 (1119) :451-465
[2]   VIOLATIONS OF HUNDS RULE IN NON-KEKULE HYDROCARBONS - THEORETICAL PREDICTION AND EXPERIMENTAL-VERIFICATION [J].
BORDEN, WT ;
IWAMURA, H ;
BERSON, JA .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (04) :109-116
[3]   Unusual Interchromophoric Interactions in β,β′ Directly and Doubly Linked Corrole Dimers: Prohibited Electronic Communication and Abnormal Singlet Ground States [J].
Cho, Sung ;
Lim, Jong Min ;
Hiroto, Satoru ;
Kim, Pyosang ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro ;
Kim, Dongho .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) :6412-6420
[4]   SPIN CONTROL IN ORGANIC-MOLECULES [J].
DOUGHERTY, DA .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (03) :88-94
[5]   THE SEARCH FOR HIGHLY COLORED ORGANIC-COMPOUNDS [J].
FABIAN, J ;
ZAHRADNIK, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (06) :677-694
[6]   Synthesis and biradicaloid character of doubly linked corrole dimers [J].
Hiroto, Satoru ;
Furukawa, Ko ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) :12380-12381
[7]   The Lowest Singlet and Triplet States of the Oxyallyl Diradical [J].
Ichino, Takatoshi ;
Villano, Stephanie M. ;
Gianola, Adam J. ;
Goebbert, Daniel J. ;
Velarde, Luis ;
Sanov, Andrei ;
Blanksby, Stephen J. ;
Zhou, Xin ;
Hrovat, David A. ;
Borden, Weston Thatcher ;
Lineberger, W. Carl .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (45) :8509-8511
[8]   STUDIES OF ORGANIC DIRADICALS, OLIGORADICALS, AND POLYRADICALS BY MEANS OF THEIR BULK MAGNETIC-PROPERTIES [J].
IWAMURA, H ;
KOGA, N .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :346-351
[9]   Interactive Radical Dimers in Photoconductive Organic Thin Films [J].
Iwasaki, Akito ;
Hu, Laigui ;
Suizu, Rie ;
Nomura, Kenji ;
Yoshikawa, Hirofumi ;
Awaga, Kunio ;
Noda, Yukiko ;
Kanai, Kaname ;
Ouchi, Yukio ;
Seki, Kazuhiko ;
Ito, Hiroshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (22) :4022-4024
[10]   Expanded porphyrins and their heterologs [J].
Jasat, A ;
Dolphin, D .
CHEMICAL REVIEWS, 1997, 97 (06) :2267-2340