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

Abstract

We designed and developed a fused-bibenzo[c]thiophene, namely, 2,9-bis(tert-butyldimethylsilyl)phenanthro[9,8-bc:10,1-b'c']dithiophene (PHDT-Si) as a new π-building block in the emitters, the photosensitizers and the semiconductors for organic optoelectronic devices. Based on photophysical (photoabsorption, fluorescence and time-resolved fluorescence spectroscopy) and electrochemical meaurement (cyclic voltammetry), and density functional theory (DFT) calculation, this work reveals that the fused-bibenzo[c]thiophene PHDT-Si which is prepared by an efficient synthetic method, has a rigid, high planar and expanded π-conjugation structure, and possesses intense photoabsorption and fluorescence properties (λmaxabs = 598 nm (εmax = 41000 M‒1 cm‒1) and λmaxfl = 613 nm (Φf = 0.74) in toluene) in long-wavelength region and electrochemically reversible oxidation process, compared to non-fused 1,1'-bis(tert-butyldimethylsilyl)-4,4'-bibenzo[c]thiophene (BBT-Si).

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

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

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