Solid-state supramolecular chirogenesis: High optical activity and gradual development of zinc octaethylporphyrin aggregates

被引：44

作者：

Borovkov, VV

Harada, T

Hembury, GA

Inoue, Y

Kuroda, R

机构：

[1] JST, ICORP, Entropy Control Project, Toyonaka, Osaka 5600085, Japan

[2] JST, ERATO, Kuroda Chiromorphol Project, Meguro Ku, Tokyo 1530041, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 15期

关键词：

chirality; circular dichroism; porphyrinoids; solid-state structures; supramolecular chemistry;

D O I：

10.1002/anie.200250524

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Slow formation of J-type helical aggregates occurs when the simple achiral zinc octaethylporphyrin interacts with enantiopure 1-cyclohexylethylamines in the solid state. These chiral solid-state aggregates exhibit a high degree of optical activity and are remarkably stable, as evidenced in the circular dichroism spectra (see picture).

引用

收藏

页码：1746 / 1749

页数：4

相关论文

共 36 条

[1] The supramolecular structure of self-assembly formed by capsanthin derivatives [J].

Bikádi, Z ;

Zsila, F ;

Deli, J ;

Mády, G ;

Simonyi, M .

ENANTIOMER, 2002, 7 (2-3) :67-76

[2] 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

[3] 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

[4] Supramolecular chirogenesis in zinc porphyrins: Equilibria, binding properties, and thermodynamics [J].

Borovkov, VV ;

Lintuluoto, JM ;

Sugeta, H ;

Fujiki, M ;

Arakawa, R ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2993-3006

[5] Stoichiometry-controlled supramolecular chirality induction and inversion in bisporphyrin systems [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

ORGANIC LETTERS, 2002, 4 (02) :169-171

[6]

Borovkov VV, 2002, ANGEW CHEM INT EDIT, V41, P1378, DOI 10.1002/1521-3773(20020415)41:8<1378::AID-ANIE1378>3.0.CO

[7]

2-L

[8] Remarkable stability and enhanced optical activity of a chiral supramolecular bis-porphyrin tweezer in both solution and solid state [J].

Borovkov, VV ;

Lintuluoto, JM ;

Sugiura, M ;

Inoue, Y ;

Kuroda, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11282-11283

[9] Temperature effect on supramolecular chirality induction in bis(zinc porphyrin) [J].

Borovkov, VV ;

Lintuluoto, JM ;

Fujiki, M ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4403-4407

[10] Supramolecular chirogenesis in zinc porphyrins: Mechanism, role of guest structure, and application for the absolute configuration determination [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :2979-2989

← 1 2 3 4 →