π-Conjugated molecules covered by permethylated cyclodextrins

Chem Rec. 2011 Sep;11(5):269-83. doi: 10.1002/tcr.201100009. Epub 2011 Sep 7.

Abstract

Insulated π-conjugated molecules, in which the π-conjugated compounds are covered by a cyclic protective sheath, have attracted considerable attention because of their potential applicability in next-generation mono-molecular electronic devices. We have developed new methods of synthesizing insulated π-conjugated molecules involving the self-inclusion of rotaxane precursors linking π-conjugated units as a guest and permethylated cyclodextrin (PMCD) as a macrocyclic host. The insulated π-conjugated molecules thus formed are highly soluble in organic solvents and display photoluminescence efficiency. This paper also highlights a new method for synthesizing insulated molecular wire (IMW) through the polymerization of insulated π-conjugated molecules as monomers. The IMWs thus formed have a high covering ratio, rigidity, and showed high charge mobility in the solid state; further, they are readily soluble in a variety of organic solvents. In this account, the synthetic methodologies and characteristic of insulated π-conjugated molecules and IMWs are discussed.

Publication types

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

MeSH terms

  • Cyclodextrins / chemical synthesis*
  • Cyclodextrins / chemistry
  • Methylation
  • Models, Molecular
  • Molecular Structure

Substances

  • Cyclodextrins