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

Hideyuki Otsuka, Takayuki Arima, Tomoyuki Koga, Atsushi Takahara

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9 Citations (Scopus)

Abstract

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 5)-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.

Original languageEnglish
Pages (from-to)957-961
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume18
Issue number9
DOIs
Publication statusPublished - Sep 1 2005

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Silicon Dioxide
Monolayers
Microscopic examination
ethyl alcohol
Enantiomers
Chirality
silicon dioxide
microscopy
Derivatives
Force measurement
Substrates
Photoelectrons
Atomic force microscopy
enantiomers
Adhesion
chirality
Ions
X rays
Molecules
2,2,2-trifluoro-1-(9-anthryl)ethanol

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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title = "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",
abstract = "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 5)-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.",
author = "Hideyuki Otsuka and Takayuki Arima and Tomoyuki Koga and Atsushi Takahara",
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T1 - Rational model for chiral recognition in a silica-based chiral column

T2 - 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

AU - Otsuka, Hideyuki

AU - Arima, Takayuki

AU - Koga, Tomoyuki

AU - Takahara, Atsushi

PY - 2005/9/1

Y1 - 2005/9/1

N2 - 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 5)-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.

AB - 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 5)-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.

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