Atomic-Scale Insight into Tautomeric Recognition, Separation, and Interconversion of Guanine Molecular Networks on Au(111)

J Am Chem Soc. 2015 Sep 16;137(36):11795-800. doi: 10.1021/jacs.5b07314. Epub 2015 Sep 4.

Abstract

Although tautomerization may directly affect the chemical or biological properties of molecules, real-space investigation on the tautomeric behaviors of organic molecules in a larger area of molecular networks has been scarcely reported. In this paper, we choose guanine (G) molecule as a model system. From the interplay of high-resolution scanning tunneling microscopy (STM) imaging and density functional theory (DFT) calculations, we have successfully achieved the tautomeric recognition, separation, and interconversion of G molecular networks (formed by two tautomeric forms G/9H and G/7H) with the aid of NaCl on the Au(111) surface in ultrahigh vacuum (UHV) conditions. Our results may serve as a prototypical system to provide important insights into tautomerization related issues, which should be intriguing to biochemistry, pharmaceutics, and other related fields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Gold / chemistry*
  • Guanine / chemistry*
  • Microscopy, Scanning Tunneling
  • Stereoisomerism

Substances

  • Guanine
  • Gold