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Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes

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.

Chemistry – A European Journal, 16 June 2014, Vol.20(25), pp.7746-7751 [Rivista Peer Reviewed]

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  • Titolo:
    Tuning Thiophene with Phosphorus: Synthesis and Electronic Properties of Benzobisthiaphospholes
  • Autore: 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.
  • Note di contenuto: 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 CH‐‐CN substituents was reduced at =−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. : Energetic tuning of conjugated building blocks can be achieved by atomic modulation of aromatic architectures. A phosphorus mimic of benzodithiophene and benzobisthiazole has been synthesized and structurally characterized (see figure). The UV/Vis spectrum of the phosphorus heterocycle is significantly redshifted compared to its organic counterparts. The redox properties of the benzobisthiaphospholes have been probed and revealed reversible reductions in THF.
  • Fa parte di: Chemistry – A European Journal, 16 June 2014, Vol.20(25), pp.7746-7751
  • Soggetti: Fused‐Ring Systems ; Heterocycles ; N‐Type Acceptors ; Organic Electronics ; Phosphorus Heterocycles
  • Lingua: Inglese
  • Tipo: Articolo
  • Identificativo: ISSN: 0947-6539 ; E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201402561

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