Electronegative Oligothiophenes for n-Type Semiconductors: Difluoromethylene-Bridged Bithiophene and Its Oligomers

The synthesis of difluoromethylene-bridged bithiophene and its oligothiophenes are reported. The spectroscopic and electrochemical measurement
as well as X-ray analyses unambiguously revealed that the difluoromethylene bridge largely contributes to keeping planarity between the
thiophene rings and lowering the LUMO level. The perfluorohexyl-substituted quaterthiophene derivatives showed n-type semiconducting
behavior with field-effect electron mobilities up to 0.018 cm2 V-1 s-1.

本文报道了二氟亚甲基桥联联噻吩（difluoromethylene-bridged bithiophene）及其低聚噻吩（oligothiophenes）的合成工作。通过光谱测试、电化学表征以及X射线分析（X-ray analyses），可明确证实：二氟亚甲基桥结构可显著维持噻吩环间的平面性，并降低最低未占据分子轨道（Lowest Unoccupied Molecular Orbital, LUMO）能级。全氟己基取代的四噻吩衍生物展现出n型半导体特性，其场效应电子迁移率最高可达0.018 cm²·V⁻¹·s⁻¹。