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Central‐to‐Axial Chirality Transfer‐Induced CD Sensor for Chiral Recognition and ee Value Detection of 1,2‐DACH Enantiomers
Author(s) -
Li Fei,
Wang Yuxiang,
Meng Fandian,
Dai Chunhui,
Cheng Yixiang,
Zhu Chengjian
Publication year - 2015
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201500236
Subject(s) - chirality (physics) , enantiopure drug , moiety , enantiomer , circular dichroism , chemistry , axial chirality , conjugated system , stereochemistry , polymer , enantioselective synthesis , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark , catalysis
The paper is mainly focused on the induced circular dichroism (ICD) based on central‐to‐axial chirality transfer for direct chiral recognition and ee value detection of 1,2‐diaminocyclohexane (1,2‐DACH) enantiomers. A novel achiral polymer sensor with potential axial chirality feature is designed and synthesized. This conjugated polymer incorporating biphenol moiety can bind chiral 1,2‐DACH substrates via intramolecular hydrogen‐bonding interactions, which could result in the detectable exciton‐coupled circular dichroism (CD) spectrum due to the chirality transfer from an enantiopure building block to a dynamically racemic 1,1′‐biphenyl‐2,2′‐diol moiety in the polymer chain backbone. The linear regression analysis of ICD sensing shows an excellent agreement between CD intensity and concentration of chiral 1,2‐DACH, which indicates this biphenol‐based achiral polymer can be used as a chiral sensor for direct recognition and ee value detection of 1,2‐DACH enantiomers by using ICD spectra of achiral polymer sensor.