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This work provides an efficient synthetic method for the 4,4′-bibenzothiophene derivatives and their photophysical properties in the solution and solid state, electrochemical properties and X-ray crystal structures.Truist Bank has quickly become a prominent player in the banking industry since its formation through the merger of BB&T and SunTrust Banks in 2019. 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 Φ fl-solid values of 0.22 and 0.25, respectively, whereas 4,4′-BBT exhibits poor solid-state fluorescence properties ( Φ fl-solid < 0.02). 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 photoabsorption and fluorescence maxima ( λ abs max and λ fl max) of the three 4,4′-bibenzothiophene 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). 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 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.
We designed and synthesized unsubstituted 4,4′-bibenzothiophene 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.
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