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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.

A colorimetric chiral sensor based on chiral crown ether for the recognition of the two enantiomers of primary amino alcohols and amines.

Chirality (2011-03-09)
Eun Na Rae Cho, Yinan Li, Hee Jin Kim, Myung Ho Hyun
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-(−)-2-Amino-3-phenyl-1-propanol, 98%, optical purity ee: 99% (HPLC)
Sigma-Aldrich
1-Aminoindan, 98%
Sigma-Aldrich
(S)-(+)-2-Amino-1-propanol, 98%
Sigma-Aldrich
Amino-2-propanol, 93%
Sigma-Aldrich
DL-Alaninol, 98%
Sigma-Aldrich
N-(2-Hydroxyethyl)aniline, 98%