Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes |
| |
| Authors: | Yunyan Qiu Joshua C Worch Danielle N Chirdon Aman Kaur Andrew B Maurer Samuel Amsterdam Christopher R Collins Prof Tomislav Pintauer Prof David Yaron Prof Stefan Bernhard Prof Kevin J T Noonan |
| |
| Affiliation: | 1. Department of Chemistry, Carnegie Mellon University, 4400 Fifth Avenue, Pittsburgh, Pennsylvania, 15213 (USA);2. Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, Pennsylvania, 15282 (USA) |
| |
| 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 E1/2=?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. |
| |
| Keywords: | fused‐ring systems heterocycles n‐type acceptors organic electronics phosphorus heterocycles |
|
|
