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A Highly Fluorinated Chiral Aldehyde for Enantioselective Fluorescent Recognition in a Biphasic System
Author(s) -
Wang Chao,
Wu Xuedan,
Pu Lin
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702354
Subject(s) - aldehyde , enantioselective synthesis , enantiomer , chemistry , methanol , fluorescence , mass spectrometry , diamine , enantiomeric excess , fluorescence spectroscopy , organic chemistry , chromatography , catalysis , physics , quantum mechanics
A 1,1′‐bi‐2‐naphthol (BINOL)‐based aldehyde containing four perfluoroalkyl groups has been designed and synthesized. It shows enantioselective fluorescence enhancement at 420 nm when treated with the enantiomers of trans ‐1,2‐diaminocyclohexane in an organic/fluorous biphasic system. The enantiomeric excess of the diamine in methanol can be linearly correlated with the emission intensity of of the aldehyde in perfluorohexane (FC‐72). This is the first example to determine the enantiomeric composition of a chiral molecule by using a fluorescent sensor in a fluorous/organic biphasic system. The mechanism of the reaction was investigated by NMR spectroscopy and mass spectrometry.