Synthesis, structure, and chemical property of the first fluorine-containing porphycene

被引:56
作者
Hayashi, T
Nakashima, Y
Ito, K
Ikegami, T
Aritome, I
Suzuki, A
Hisaeda, Y [1 ]
机构
[1] Kyushu Univ, Grad Sch Engn, Dept Biochem & Chem, Fukuoka 8128581, Japan
[2] Nagaoka Natl Coll Technol, Dept Mat Engn, Nagaoka, Niigata 9408532, Japan
关键词
D O I
10.1021/ol0348452
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Graphics A pyrrolic macrocycle, beta-tetrakis(trifluoromethyl)porphycene, is the first example of a fluorine-containing porphycene. Four electron-withdrawing CF3 substituents provide a highly distorted structure and an attractive electron-deficient nature for the porphycene framework. From the electrochemical study, it is found that the LUMO energy level for the beta-trifluoromethylporphycene is 1.24 V more stabilized compared to that for etioporphyrin. Moreover, the deprotonation of the inner N-H proton in the porphycene was observed upon the addition of DBU.
引用
收藏
页码:2845 / 2848
页数:4
相关论文
共 30 条
[1]   3,6,13,16-tetrabromo-2,7,12,17-tetrapropylporphycene [J].
Aritome, I ;
Shimakoshi, H ;
Hisaeda, Y .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2002, 58 (09) :O563-O564
[2]   REDOX PROPERTIES OF PORPHYCENES AND METALLOPORPHYCENES - A COMPARISON WITH PORPHYRINS [J].
BERNARD, C ;
GISSELBRECHT, JP ;
GROSS, M ;
VOGEL, E ;
LAUSMANN, M .
INORGANIC CHEMISTRY, 1994, 33 (11) :2393-2401
[3]   F-19 NMR-SPECTRA AND STRUCTURES OF HALOGENATED PORPHYRINS [J].
BIRNBAUM, ER ;
HEDGE, JA ;
GRINSTAFF, MW ;
SCHAEFER, WP ;
HENLING, L ;
LABINGER, JA ;
BERCAW, JE ;
GRAY, HB .
INORGANIC CHEMISTRY, 1995, 34 (14) :3625-3632
[4]   Electronic, spectral, and electrochemical properties of (TPPBrx)Zn where TPPBrx is the dianion of β-brominated-pyrrole tetraphenylporphyrin and x varies from 0 to 8 [J].
D'Souza, F ;
Zandler, ME ;
Tagliatesta, P ;
Ou, ZP ;
Shao, JG ;
Van Caemelbecke, E ;
Kadish, KM .
INORGANIC CHEMISTRY, 1998, 37 (18) :4567-4572
[5]   Polyhaloporphyrins: Unusual ligands for metals and metal-catalyzed oxidations [J].
Dolphin, D ;
Traylor, TG ;
Xie, LY .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (06) :251-259
[6]   REDOX PROPERTIES OF PORPHYCENES AND METALLOPORPHYCENES AS COMPARED WITH PORPHYRINS [J].
GISSELBRECHT, JP ;
GROSS, M ;
KOCHER, M ;
LAUSMANN, M ;
VOGEL, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8618-8620
[7]   Synthesis, structure, electronic spectroscopy, photophysics, electrochemistry, and x-ray photoelectron spectroscopy of highly-electron-deficient [5,10,15,20-tetrakis(perfluoroalkyl)porphinato]zinc(II) complexes and their free base derivatives [J].
Goll, JG ;
Moore, KT ;
Ghosh, A ;
Therien, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8344-8354
[8]  
Guilard R, 1995, SYNTHESIS-STUTTGART, P1480
[9]   ELECTROCHEMISTRY OF NONPLANAR ZINC(II) TETRAKIS(PENTAFLUOROPHENYL)PORPHYRINS [J].
HODGE, JA ;
HILL, MG ;
GRAY, HB .
INORGANIC CHEMISTRY, 1995, 34 (04) :809-812
[10]   ELECTRON DEFICIENT PORPHYRINS .1. TETRAKIS(TRIFLUOROMETHYL)PORPHYRIN AND ITS METAL-COMPLEXES [J].
HOMMA, M ;
AOYAGI, K ;
AOYAMA, Y ;
OGOSHI, H .
TETRAHEDRON LETTERS, 1983, 24 (40) :4343-4346