title: Tuning thiophene with phosphorus: synthesis and electronic properties of benzobisthiaphospholes.
abstract: 1,4-Dimercapto-2,5-diphosphinobenzene and 3,6-bis(hexyloxy)-1,4-dimercapto-2,5-diphosphinobenzene were synthesized and combined with various acid chlorides to obtain a series of benzobisthiaphospholes. Electrochemical and photophysical properties of the substituted benzobisthiaphospholes have been evaluated, and the observed reductions are more facile than the related benzothiaphospholes and 2,6-diphenylbenzobisthiazole. A benzobisthiaphosphole with C6H4-p-CN substituents was reduced at E(1/2)=-1.08 V (vs. saturated calomel electrode (SCE)). X-ray diffraction data for several of these phosphorus heterocycles has been obtained, and DFT calculations at the B3LYP level have been performed.
authors.affiliation: Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania, 15213 (USA).
authors.forename: Yunyan
authors.initials: Y
authors.lastname: Qiu
authors.forename: Joshua C
authors.initials: JC
authors.lastname: Worch
authors.forename: Danielle N
authors.initials: DN
authors.lastname: Chirdon
authors.forename: Aman
authors.initials: A
authors.lastname: Kaur
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Maurer
authors.forename: Samuel
authors.initials: S
authors.lastname: Amsterdam
authors.forename: Christopher R
authors.initials: CR
authors.lastname: Collins
authors.forename: Tomislav
authors.initials: T
authors.lastname: Pintauer
authors.forename: David
authors.initials: D
authors.lastname: Yaron
authors.forename: Stefan
authors.initials: S
authors.lastname: Bernhard
authors.forename: Kevin J T
authors.initials: KJ
authors.lastname: Noonan
keywords: fused-ring systems; heterocycles; n-type acceptors; organic electronics; phosphorus heterocycles