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Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes
Author(s) -
Qiu Yunyan,
Worch Joshua C.,
Chirdon Danielle N.,
Kaur Aman,
Maurer Andrew B.,
Amsterdam Samuel,
Collins Christopher R.,
Pintauer Tomislav,
Yaron David,
Bernhard Stefan,
Noonan Kevin J. T.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402561
Subject(s) - thiophene , electrochemistry , saturated calomel electrode , phosphorus , chemistry , diffraction , electrode , organic chemistry , reference electrode , physics , optics
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 C 6 H 4 ‐ 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.