Ooyama Yousuke, Enoki Toshiaki, Aoyama Satoshi, Ohshita Joji
Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima 739-8527, Japan.
Org Biomol Chem. 2017 Sep 13;15(35):7302-7307. doi: 10.1039/c7ob01695f.
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, 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 (λ = 598 nm (ε = 41 000 M cm) and λ = 613 nm (Φ = 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).
我们设计并开发了一种稠合联苯并[c]噻吩，即2,9-双(叔丁基二甲基硅基)菲并[9,8-bc:10,1-b'c']二噻吩(PHDT-Si)，作为用于有机光电器件的发光体、光敏剂和半导体中的一种新型π-结构单元。基于光物理(光吸收、荧光和时间分辨荧光光谱)和电化学测量(循环伏安法)以及密度泛函理论(DFT)计算，这项工作表明，通过高效合成方法制备的稠合联苯并[c]噻吩PHDT-Si具有刚性、高平面性和扩展的π-共轭结构，并且在长波长区域具有强烈的光吸收和荧光特性(在甲苯中λ = 598 nm(ε = 41000 M cm)和λ = 613 nm(Φ = 0.74))，并且与未稠合的1,1'-双(叔丁基二甲基硅基)-4,4'-联苯并[c]噻吩(BBT-Si)相比，经历了一个电化学可逆氧化过程。
