Enantioselective adsorption of phenylalanine onto self-assembled monolayers of 1,1'binaphthalene-2,2'-dithiol on gold

Takuya Nakanishi; Naoko Yamakawa; Toru Asahi; Tetsuya Osaka; Bunsho Ohtani; Kohei Uosaki

doi:10.1021/ja012084x

Enantioselective adsorption of phenylalanine onto self-assembled monolayers of 1,1'binaphthalene-2,2'-dithiol on gold

J Am Chem Soc. 2002 Feb 6;124(5):740-1. doi: 10.1021/ja012084x.

Authors

Takuya Nakanishi¹, Naoko Yamakawa, Toru Asahi, Tetsuya Osaka, Bunsho Ohtani, Kohei Uosaki

Affiliation

¹ Department of Applied Chemistry, School of Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan.

PMID: 11817935
DOI: 10.1021/ja012084x

Abstract

Self-assembled monolayer of atropisomeric compound, 1,1'-binaphthalene-2,2'-dithiol (BNSH), provides a field for chiral discrimination. The two-dimensional chiral arrangement with screw-like units, each of which is composed of three BNSH molecules, plays an important role in the enantioselectivity of adsorption of phenylalanine, as revealed by a quartz crystal microbalance technique.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adsorption
Gold / chemistry*
Naphthalenes / chemistry*
Phenylalanine / chemistry*
Stereoisomerism
Substrate Specificity
Surface Properties

Substances

1,1'-bianphthalene-2,2'-dithiol
Naphthalenes
Phenylalanine
Gold