Li Bingbing, Zhang Sheng, Li Lu, Ma Zhiying, Li Chunli, Xu Li, Wang Hua
Engineering Research Center for Nanomaterials and College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.
School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, P. R. China.
ACS Omega. 2018 Nov 27;3(11):16014-16020. doi: 10.1021/acsomega.8b02492. eCollection 2018 Nov 30.
The all-thiophene-based double helix was designed and prepared originally from the selective deprotonation of cyclooctatetrathiophene (tetra[3,4]thienylene, ) and following the Negishi coupling reaction with 3,3'-bithiophene. The X-ray crystallographic studies revealed that has a double-helical scaffold. The arylations including tetraphenylation and tetrathienylation were efficiently employed to replace the four α-protons of the central of with phenyl and thiophenyl groups via cross-coupling reactions. The chiral resolution of - was fulfilled via chiral high-performance liquid chromatography, and the chiroptical properties were characterized by circular dichroism spectra and optical rotation. Ultraviolet-visible absorption and fluorescence behaviors of and its arylation products were also characterized to describe the extended conjugated scaffold.
全噻吩基双螺旋最初是通过环辛四噻吩（四[3,4]噻吩撑）的选择性去质子化并随后与3,3'-联噻吩进行根岸偶联反应而设计和制备的。X射线晶体学研究表明，其具有双螺旋支架。包括四苯基化和四噻吩基化在内的芳基化反应通过交叉偶联反应有效地用于用苯基和噻吩基取代中心环辛四噻吩的四个α-质子。通过手性高效液相色谱法实现了其对映体拆分，并通过圆二色光谱和旋光对其手性光学性质进行了表征。还对其及其芳基化产物的紫外可见吸收和荧光行为进行了表征，以描述扩展的共轭支架。
