Rationalization of supramolecular chirality in a bisporphyrin system

被引:77
作者
Borovkov, VV
Fujii, I
Muranaka, A
Hembury, GA
Tanaka, T
Ceulemans, A
Kobayashi, N
Inoue, Y
机构
[1] JST, ICORP, Entropy Control Project, Toyonaka, Osaka 5600085, Japan
[2] Tokai Univ, Dept Biol Sci & Technol, Shizuoka 4100321, Japan
[3] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
[4] Kobe Univ, Grad Sch Sci & Technol, Dept Biosyst Sci, Kobe, Hyogo 6578501, Japan
[5] Katholieke Univ Leuven, Div Quantum Chem, B-3001 Heverlee, Belgium
关键词
chirality; circular dichroism; porphyrinoids; structure elucidation; supramolecular chemistry;
D O I
10.1002/anie.200460965
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A sign of the times: A 1:1 tweezer complex consisting of an achiral bis(zinc porphyrin) and (R,R)-1,2-diaminocyclohexane has been characterized by X-ray crystallographic analysis (see picture, Zn red, N blue). This has enabled a full and unambiguous rationalization of the highly efficient transfer of chirality information from an optically active guest to an achiral host in a supramolecular system based on a bisporphyrin to be carried out.
引用
收藏
页码:5481 / 5485
页数:5
相关论文
共 66 条
[1]  
Balaban T. S., 2003, ANGEW CHEM, V115, P2190, DOI 10.1002/ange.200250465
[2]   Controlling chirality and optical properties of artificial antenna systems with self-assembling porphyrins [J].
Balaban, TS ;
Bhise, AD ;
Fischer, M ;
Linke-Schaetzel, M ;
Roussel, C ;
Vanthuyne, N .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (19) :2140-2144
[3]  
Berova N., 2000, Circular Dichroism: Principles and Applications
[4]   DETERMINATION OF THE ABSOLUTE CONFIGURATION OF OPTICALLY ACTIVE COMPOUNDS BY MEANS OF X-RAYS [J].
BIJVOET, JM ;
PEERDEMAN, AF ;
VANBOMMEL, AJ .
NATURE, 1951, 168 (4268) :271-272
[5]   Elucidation of the mechanism of supramolecular chirality inversion in bis(zinc porphyrin) by dynamic approach using CD and 1H NMR spectroscopy [J].
Borovkov, VV ;
Lintuluoto, JM ;
Inone, Y .
JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (40) :9213-9219
[6]   Supramolecular chirogenesis in bis(zinc porphyrin): An absolute configuration probe highly sensitive to guest structure [J].
Borovkov, VV ;
Lintuluoto, JM ;
Inoue, Y .
ORGANIC LETTERS, 2000, 2 (11) :1565-1568
[7]  
Borovkov VV, 1999, HELV CHIM ACTA, V82, P919, DOI 10.1002/(SICI)1522-2675(19990609)82:6<919::AID-HLCA919>3.0.CO
[8]  
2-P
[9]   Origin, control, and application of supramolecular chirogenesis in bisporphyrin-based systems [J].
Borovkov, VV ;
Hembury, GA ;
Inoue, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (07) :449-459
[10]   The origin of solvent-controlled supramolecular chirality switching in a Bis(Zinc porphyrin) system [J].
Borovkov, VV ;
Hembury, GA ;
Inoue, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5310-5314