Hg 2+ ‐Induced In Situ Generated Radical Cation of ( S )‐BINOL‐Based Polymer for Highly Enantioselective Recognition of Phenylalaninol

Phenylalaninol enantiomers are one of the most important chiral compounds due to its presence in biologically active molecules and pharmaceutical products. In this paper, a novel chiral fluorescence polymer sensor incorporating ( S )‐BINOL and oligomeric aniline via a nucleophilic addition–eliminati...

Full description

Saved in:
Bibliographic Details
Published in:Macromolecular rapid communications. 2014-08, Vol.35 (16), p.1443-1449
Main Authors: Jiao, Jiemin, Li, Fei, Zhang, Shuwei, Quan, Yiwu, Zheng, Wenhua, Cheng, Yixiang, Zhu, Chengjian
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Phenylalaninol enantiomers are one of the most important chiral compounds due to its presence in biologically active molecules and pharmaceutical products. In this paper, a novel chiral fluorescence polymer sensor incorporating ( S )‐BINOL and oligomeric aniline via a nucleophilic addition–elimination reaction is designed and synthesized. Polymer sensor exhibits “turn‐off” fluorescence quenching response upon the addition of Hg 2+ , and “turn‐on” moderate fluorescence enhancement behavior towards phenylalaninol enantiomers. Meanwhile, this kind of ( S )‐BINOL‐based polymer sensor can exhibit highly selective enantioselective recognition response towards ( L )‐phenylalaninol upon the addition of Hg 2+ and the value of ef can reach as high as 5.4, which can be attributed to the formation of in situ generated radical cation arisen from oligomeric aniline moiety by Hg 2+ induction. image
ISSN:1022-1336
1521-3927
DOI:10.1002/marc.201400248