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Synthesis and optical and electrochemical properties of a phenanthrodithiophene (fused-bibenzo[c]thiophene) derivative

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Abstract

We designed and developed a fused-bibenzo[c]thiophene, namely, 2,9-bis(tert-butyldimethylsilyl)phenanthro[9,8-bc:10,1-bc′]dithiophene (PHDT-Si), as a new π-building block in the emitters, photosensitizers and semiconductors for organic optoelectronic devices. Based on photophysical (photoabsorption, fluorescence and time-resolved fluorescence spectroscopy) and electrochemical measurements (cyclic voltammetry), and density functional theory (DFT) calculations, this work reveals that the fused-bibenzo[c]thiophene PHDT-Si, which is prepared by an efficient synthesis method, has a rigid, high planar and expanded π-conjugation structure, and possesses intense photoabsorption and fluorescence properties (λabsmax = 598 nm (εmax = 41 000 M−1 cm−1) and λflmax = 613 nm (Φf = 0.74) in toluene) in the long-wavelength region and undergoes an electrochemically reversible oxidation process, compared to non-fused 1,1′-bis(tert-butyldimethylsilyl)-4,4′-bibenzo[c]thiophene (BBT-Si).

Graphical abstract: Synthesis and optical and electrochemical properties of a phenanthrodithiophene (fused-bibenzo[c]thiophene) derivative

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Publication details

The article was received on 10 Jul 2017, accepted on 08 Aug 2017 and first published on 08 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01695F
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis and optical and electrochemical properties of a phenanthrodithiophene (fused-bibenzo[c]thiophene) derivative

    Y. Ooyama, T. Enoki, S. Aoyama and J. Ohshita, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01695F

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