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Rational model for chiral recognition in a silica‐based chiral column: chiral recognition of N ‐(3,5‐dinitrobenzoyl)phenylglycine‐terminated alkylsilane monolayer by 2,2,2‐trifluoro‐1‐(9‐anthryl)ethanol derivatives by chemical force microscopy
Author(s) -
Otsuka Hideyuki,
Arima Takayuki,
Koga Tomoyuki,
Takahara Atsushi
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.934
Subject(s) - chemistry , enantiomer , chirality (physics) , monolayer , molecule , substrate (aquarium) , cantilever , analytical chemistry (journal) , stereochemistry , chromatography , crystallography , organic chemistry , chemical engineering , composite material , biochemistry , chiral symmetry breaking , physics , oceanography , materials science , quantum mechanics , geology , nambu–jona lasinio model , quark , engineering
Direct measurement of the chemical force between chiral molecules was investigated by chemical force microscopy (CFM). 2,2,2‐Trifluoro‐1‐(9‐anthryl)ethanol (TFAE) and N ‐(3,5‐dinitrobenzoyl)phenylglycine (DNBP), a well‐known pair of enantiomers, were strongly immobilized on the surface of the cantilever tip and the substrate surface, respectively, by the use of aminosilane, to propose a chiral stationary phase model system of a silica‐based chiral column. The modification of TFAE on a cantilever tip and DNBP on the substrate surface was confirmed by x‐ray photoelectron spectroscopic and time‐of‐flight secondary ion mass spectrometric measurements. The force curve between ( R or S )‐TFAE and ( R or S )‐DNBP enantiomers were measured using the force measurement mode scanning force microscopy to determine the magnitude of the interaction. The histograms of the adhesion force for a different chirality pair [( R )‐ATEA vs ( S )‐DNBP and ( S )‐ATEA vs ( R )‐DNBP] showed a broader distribution than those for the identical chirality pair [( R )‐ATEA vs ( R )‐DNBP and ( S )‐ATEA vs ( S )‐DNBP]. Since CFM measurement cans recognize the difference of in nanonewton forces, the results can be regarded as a rational design for chiral recognition in a silica‐based chiral column. Copyright © 2005 John Wiley & Sons, Ltd.