Homochiral Self-Sorting During Macrocycle Formation and their Chiroptical Properties.

IF 2.5 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemistryOpen Pub Date : 2024-11-26 DOI:10.1002/open.202400400

Diptiprava Sahoo, Soumen De

引用次数: 0

Abstract

Several BINOL-derived C2-symmetric aldehydes were synthesized to investigate chiral self-sorting phenomena during macrocycle formation in the presence of aliphatic and aromatic bisamines. While self-sorting was unsuccessful with aliphatic amines, aromatic amine dictated complete homochiral self-sorting, confirmed by ¹H NMR analysis and molecular modelling. Additionally, the impact of macrocyclization on the chiroptical properties of these macrocycles was examined. The Cotton effects band red-shifted for aromatic amines owing to extended conjugation. Notably, a substantial increase in specific rotation was observed upon macrocycle formation.

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大环形成过程中的同手性自排序及其奇光特性

我们合成了几种 BINOL 衍生的 C2 对称醛，以研究在脂肪族和芳香族双胺存在下，大环形成过程中的手性自排序现象。虽然脂肪族胺的自排序不成功，但芳香族胺却能实现完全的同手性自排序，这一点已通过 1H NMR 分析和分子建模得到证实。此外，我们还研究了大环化对这些大环的光电性质的影响。由于扩展共轭，芳香胺的科顿效应带发生了红移。值得注意的是，在形成大环后，观察到比旋显著增加。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.80

自引率

4.30%

发文量

143

审稿时长

1 months

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