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A colorimetric chiral sensor based on chiral crown ether for the recognition of the two enantiomers of primary amino alcohols and amines
Author(s) -
Cho Eun Na Rae,
Li Yinan,
Kim Hee Jin,
Hyun Myung Ho
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20928
Subject(s) - chemistry , enantiomer , chirality (physics) , crown ether , chiral derivatizing agent , chromophore , primary (astronomy) , ether , stereochemistry , organic chemistry , chiral column chromatography , chiral symmetry , ion , physics , quantum mechanics , astronomy , nambu–jona lasinio model , quark
A new colorimetric chiral sensor material consisting of three different functional sites such as chromophore (2,4‐dinitrophenylazophenol dye), binding site (crown ether), and chiral barrier (3,3′‐diphenyl‐1,1′‐binaphthyl group) was prepared and applied to the recognition of the two enantiomers of primary amino alcohols and amines. Among five primary amino alcohols and two primary amines tested, the two enantiomers of phenylalaninol show the highest difference in the absorption maximum wavelength (Δλ max = 43.5 nm) and in the association constants ( K S / K R = 2.51) upon complexation with the colorimetric chiral sensor material and, consequently, the two enantiomers of phenylalaninol were clearly distinguished from each other by the color difference. Chirality, 2011. © 2010 Wiley‐Liss, Inc.