Supramolecular chirogenesis in bis(zinc porphyrin): An absolute configuration probe highly sensitive to guest structure

被引:55
作者
Borovkov, VV [1 ]
Lintuluoto, JM [1 ]
Inoue, Y [1 ]
机构
[1] JSY, ERATO, Inoue Photochirogenesis Project, Toyonaka, Osaka 5600085, Japan
关键词
D O I
10.1021/ol0000556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The role of the ligand's structure and absolute configuration in the supramolecular chirality induction in achiral bis(zinc porphyrin) has been studied. The amines with bulkier substituents resulted in stronger CD signals due to increased helical displacement in the anti conformer. All the amines with an R absolute configuration gave a negative first Cotton effect and positive second Cotton effect, while the ligands with an S absolute configuration produced CD signals with opposite signs due to formation of the left and right-handed screw diastereomers, respectively.
引用
收藏
页码:1565 / 1568
页数:4
相关论文
共 23 条
  • [21] Strong enhancement of nonlinear optical properties through supramolecular chirality
    Verbiest, T
    Van Elshocht, S
    Kauranen, M
    Hellemans, L
    Snauwaert, J
    Nuckolls, C
    Katz, TJ
    Persoons, A
    [J]. SCIENCE, 1998, 282 (5390) : 913 - 915
  • [22] Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexation
    Yashima, E
    Matsushima, T
    Okamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) : 6345 - 6359
  • [23] Memory of macromolecular helicity assisted by interaction with achiral small molecules
    Yashima, E
    Maeda, K
    Okamoto, Y
    [J]. NATURE, 1999, 399 (6735) : 449 - 451