Amidourea-based hydrogen-bonded heteroduplexes: structure and assembling selectivity

J Org Chem. 2012 Sep 21;77(18):7815-22. doi: 10.1021/jo301434a. Epub 2012 Sep 4.

Abstract

A new class of multiply hydrogen-bonded heteroduplexes from readily available amidourea derivatives was designed, and their structures and selective assembling behaviors were investigated. Amidourea derivative 3 could selectively assemble with 1 to form a stable heteroduplex via eight intermolecular bifurcated hydrogen bonds, but could not assemble with 2 at all, because of their unique structures and the spacing effect, although 1 and 2 possessed the same hydrogen-bonding sequence. The high stability and selectivity will make the amidourea-based hydrogen-bonded heteroduplexes be potentially applicable in the design of well-defined supramolecular architectures and novel functional materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding*
  • Macromolecular Substances / chemical synthesis*
  • Macromolecular Substances / chemistry*
  • Models, Molecular
  • Urea / analogs & derivatives*
  • Urea / chemistry*

Substances

  • Macromolecular Substances
  • Urea