title: Reverse selectivity in m-CPBA oxidation of oligothiophenes to sulfones.
abstract: Oligothiophene sulfones of up to six rings can be conveniently prepared by the direct oxidation of butyl-substituted thiophene oligomers with m-CPBA in dichloromethane. Reverse selectivity of oxidized rings is observed relative to previously reported systems without beta-substitution. The selectivity in the trimer and hexamer is confirmed with single-crystal X-ray structure data. The sulfones possess red-shifted absorptions and increased electron affinities relative to the parent oligomers.
authors: Division of Science and Mathematics, University of Minnesota, Morris, Minnesota 56267, USA. pappe001@morris.umn.edu
authors: Ted M
authors: TM
authors: Pappenfus
authors: Jacob H
authors: JH
authors: Melby
authors: Brent B
authors: BB
authors: Hansen
authors: Devin M
authors: DM
authors: Sumption
authors: Scott A
authors: SA
authors: Hubers
authors: Daron E
authors: DE
authors: Janzen
authors: Paul C
authors: PC
authors: Ewbank
authors: Kari A
authors: KA
authors: McGee
authors: Michael W
authors: MW
authors: Burand
authors: Kent R
authors: KR
authors: Mann
mesh_terms: D002723:Chlorobenzoates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004563:Electrochemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D002723:Chlorobenzoates; D013450:Sulfones; D013876:Thiophenes; C000433:3-chloroperbenzoic acid