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Issue 31, 2021, Issue in Progress
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Synthesis, optical and electrochemical properties of 4,4′-bibenzo[c]thiophene derivatives

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Abstract

We designed and synthesized unsubstituted 4,4′-bibenzo[c]thiophene 4,4′-BBT and its silyl-substituted derivatives 1,1′-Si-4,4′-BBT and 1,1′,3,3′-Si-4,4′-BBT with one or two tert-butyldimethylsilyl groups on each thiophene ring, as new π-building blocks in emitters, photosensitizers and semiconductors for organic optoelectronic devices. The characterization of 4,4′-BBT, 1,1′-Si-4,4′-BBT and 1,1′,3,3′-Si-4,4′-BBT was successfully determined by FTIR, 1H and 13C NMR measurements, high-resolution mass spectrometry (HRMS) analysis, photoabsorption and fluorescence spectroscopy, cyclic voltammetry (CV) and density functional theory (DFT) calculations. Moreover, a single-crystal X-ray structural analysis was successfully made for 1,1′-Si-4,4′-BBT and 1,1′,3,3′-Si-4,4′-BBT. The photoabsorption and fluorescence maxima (λabsmax and λflmax) of the three 4,4′-bibenzo[c]thiophene derivatives in toluene exhibit bathochromic shifts in the order of 4,4′-BBT (359 nm and 410 nm) < 1,1′-Si-4,4′-BBT (366 nm and 420 nm) < 1,1′,3,3′-Si-4,4′-BBT (371 nm and 451 nm). The HOMO and LUMO energy levels rise in the order of 4,4′-BBT (−5.55 eV and −2.39 eV) < 1,1′-Si-4,4′-BBT (−5.45 eV and −2.34 eV) < 1,1′,3,3′-Si-4,4′-BBT (−5.34 eV and −2.30 eV), but the rise of the HOMO energy level is larger than that of the LUMO energy level, resulting in the bathochromic shift of the photoabsorption band from 4,4′-BBT to 1,1′,3,3′-Si-4,4′-BBT. The fluorescence quantum yields (Φfl) of 4,4′-BBT, 1,1′-Si-4,4′-BBT and 1,1′,3,3′-Si-4,4′-BBT in toluene are 0.41, 0.41 and 0.36, respectively. It is worth mentioning that in the solid state 1,1′-Si-4,4′-BBT and 1,1′,3,3′-Si-4,4′-BBT show relatively high Φfl-solid values of 0.22 and 0.25, respectively, whereas 4,4′-BBT exhibits poor solid-state fluorescence properties (Φfl-solid < 0.02). This work provides an efficient synthetic method for the 4,4′-bibenzo[c]thiophene derivatives and their photophysical properties in the solution and solid state, electrochemical properties and X-ray crystal structures.

Graphical abstract: Synthesis, optical and electrochemical properties of 4,4′-bibenzo[c]thiophene derivatives

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Article information


Submitted
13 Feb 2021
Accepted
19 May 2021
First published
25 May 2021

This article is Open Access

RSC Adv., 2021,11, 18870-18880
Article type
Paper

Synthesis, optical and electrochemical properties of 4,4′-bibenzo[c]thiophene derivatives

K. Obayashi, K. Imato, S. Aoyama, T. Enoki, S. Akiyama, M. Ishida, S. Suga, K. Mitsudo and Y. Ooyama, RSC Adv., 2021, 11, 18870
DOI: 10.1039/D1RA01189H

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