Synthesis and Characterization of Soluble Low-Bandgap Oligothiophene- [all]-S,S-dioxides-Based Conjugated Oligomers and Polymers

ABSTRACT: The synthesis and characterization of a new family of soluble oligothiophene-S,S-dioxides and their use as build-ing blocks to form polythiophene-S,S-dioxides via microwave-assisted Stille coupling polymerization are described. Incorpo-ration of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene-S,S-diox-ide are lower with respect to polythiophenes, this tendency is considerably stronger for the lowest unoccupied molecular orbital than for the highest occupied molecular orbital, result-ing in greater electron-accepting ability. VC 2011 Wiley Periodi