A new entry to doubly N-confused [26]hexaphyrins(1.1.1.1.1.1) from normal [26]hexaphyrins(1.1.1.1.1.1) through an unprecedented double pyrrolic rearrangement

被引:66
作者
Suzuki, M
Yoon, MC
Kim, DY
Kwon, JH
Furuta, H [1 ]
Kim, D
Osuka, A
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[2] CREST, Japan Sci & Technol Agcy, Kyoto 6068502, Japan
[3] Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8128581, Japan
[4] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
[5] Yonsei Univ, Ctr Ultrafast Opt Characterist Control, Seoul 120749, South Korea
关键词
porphyrinoids; pyrrole rearrangement; structure elucidation; transition metals;
D O I
10.1002/chem.200501061
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of hexakis (pentafluorophenyl)-substituted [26]hexaphyrin(1.1.1.1.1.1) (1) with CuCl in the presence of pyridine and molecular oxygen led to formation of doubly N-confused [26]hexaphyrin(1.1.1.1.1.1) 2 in a moderate yield through an unprecedented double pyrrolic rearrangement. Macrocycle 2 has been shown to serve as an effective bis-metal-coordinating ligand and exhibits attractive optical properties such as a sharp Soret-like band at 566 nm and low-energy fluorescence at 1058 nm.
引用
收藏
页码:1754 / 1759
页数:6
相关论文
共 44 条
[1]   Comparative photophysics of [26]- and [28]hexaphyrins(1.1.1.1.1.1): Large two-photon absorption cross section of aromatic [26]hexaphyrins(1.1.1.1.1.1) [J].
Ahn, TK ;
Kwon, JH ;
Kim, DY ;
Cho, DW ;
Jeong, DH ;
Kim, SK ;
Suzuki, M ;
Shimizu, S ;
Osuka, A ;
Kim, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (37) :12856-12861
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], ANGEW CHEM
[4]   Receptor-targeted optical imaging of tumors with near-infrared fluorescent ligands [J].
Becker, A ;
Hessenius, C ;
Licha, K ;
Ebert, B ;
Sukowski, U ;
Semmler, W ;
Wiedenmann, B ;
Grötzinger, C .
NATURE BIOTECHNOLOGY, 2001, 19 (04) :327-331
[5]   TETRA-P-TOLYLPORPHYRIN WITH AN INVERTED PYRROLE RING - A NOVEL ISOMER OF PORPHYRIN [J].
CHMIELEWSKI, PJ ;
LATOSGRAZYNSKI, L ;
RACHLEWICZ, K ;
GLOWIAK, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (07) :779-781
[6]  
CHMIELEWSKI PJ, 1994, ANGEW CHEM, V106, P805
[7]   PORPHOCYANINE - AN EXPANDED TETRAPYRROLIC MACROCYCLE [J].
DOLPHIN, D ;
RETTIG, SJ ;
TANG, H ;
WIJESEKERA, T ;
XIE, LY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9301-9302
[8]   NEAR-INFRARED ABSORBING DYES [J].
FABIAN, J ;
NAKAZUMI, H ;
MATSUOKA, M .
CHEMICAL REVIEWS, 1992, 92 (06) :1197-1226
[9]   Confusion, inversion, and creation - a new spring from porphyrin chemistry [J].
Furuta, H ;
Maeda, H ;
Osuka, A .
CHEMICAL COMMUNICATIONS, 2002, (17) :1795-1804
[10]   N-CONFUSED PORPHYRIN - A NEW ISOMER OF TETRAPHENYLPORPHYRIN [J].
FURUTA, H ;
ASANO, T ;
OGAWA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :767-768