An efficient, modular synthetic route to oligomers based on zirconocene coupling: Properties for phenylene-thiophene-1-oxide and phenylene-thiophene-1,1-dioxide chains

Narrow band gaps and high electron affinities are associated with the new oligomers containing thiophene-1-oxide and thiophene-dioxide that have been prepared by zirconocene coupling methods. A series of oligomers with 3-11 rings (X=2H, S, and S(=0)₂; see picture) allow the electronic properties of conjugated chains to be investigated. Of particular note is that the less electronic-withdrawing sulfoxide group results in the narrowest band gap.