Efficient synthesis, structure, and complexation studies of electron-donating thiacalix[n]dithienothiophene

Angew Chem Int Ed Engl. 2015 Feb 23;54(9):2734-8. doi: 10.1002/anie.201410970. Epub 2015 Jan 16.

Abstract

A series of thiacalix[n]dithiothiophenes (n=4-10) was prepared by a facile method and X-ray analysis was used to determine the molecular structures of square- (4-mer) and pentagonal-shaped macrocycles (5-mer). In the cyclic voltammograms, reversible multielectron redox processes, which are due to electronic delocalization, were observed at low oxidation potentials. The cyclic 4-mer acted as a "Janus-head" cavitand for two C60 molecules, whereas the 5- and 6-mer formed stable 1:1 complexes with C60 .

Keywords: cross-coupling; electrochemistry; macrocycles; sulfur heterocycles; supramolecular chemistry.