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

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.