Adsorption-induced asymmetric assembly from an achiral adsorbate

被引：34

作者：

Cai, YG ^{[1
]}

Bernasek, SL ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08540 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 43期

关键词：

D O I：

10.1021/ja045769g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Symmetry breaking in the self-assembled monolayer (SAM) structure of 1-octadecanol on highly ordered pyrolytic graphite (HOPG) is observed. Due to the slight mismatch of the octadecanol molecule with the graphite lattice, the alkane chain undergoes distortion upon adsorption on the surface. The asymmetric distortion of the octadecanol SAM unit cell pair is observed by scanning tunneling microscopy at the liquid/solid interface. Asymmetric distortion is due to the requirement for planarity of the hydrogen bond connecting the two octadecanol molecules in the chevron-shaped unit cell. This very simple structure provides the first example of an adsorption-induced distortion to form a supramolecular asymmetric structure, which is formed by achiral molecules adsorbed on an achiral surface. What makes this system interesting and different from other examples of adsorption-induced chirality is that the adsorbate itself undergoes asymmetric distortion due to the existence of the substrate and the adsorbate conformation is different from the molecule in solution.

引用

页码：14234 / 14238

页数：5

共 39 条

[1] ENANTIOSELECTIVE SYNTHESIS USING CHIRAL HETEROGENEOUS CATALYSTS [J].