Furo-Fused BINOL Based Crown as a Fluorescent Chiral Sensor for Enantioselective Recognition of Phenylethylamine and Ethyl Ester of Valine

A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a flourescence enhance...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-07, Vol.72 (15), p.5709-5714
Main Authors: Upadhyay, Sunil P, Pissurlenkar, Raghuvir R. S, Coutinho, Evans C, Karnik, Anil V
Format: Article
Language:English
Subjects:
Chemistry
Crown Ethers - chemistry
Esters
Exact sciences and technology
Fluorescent Dyes - chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Magnetic Resonance Spectroscopy
Mass Spectrometry
Models, Molecular
Organic chemistry
Phenethylamines - chemistry
Preparations and properties
Spectrometry, Fluorescence
Stereoisomerism
Valine - chemistry
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Summary:A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a flourescence enhancement difference of 2.97 times between two enantiomers of phenylethylamine and 2.55 times between two enantiomers of ethyl ester of valine. The ratio of association constants for two diastereomeric complexes of two enantiomers of phenylethylamine was found to be 11.30, and the ratio for two enantiomers of ethyl ester of valine was 7.02.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070850y