To explore the effect of hydrogen bonding on organic semiconductors, four novel benzo[b]thiophene-benzo[b]furan analogues with contorted configuration were synthesized and exhibited good solubility in normal solvents. The optical, electrochemical characteristics and DFT simulated calculations demonstrates that the configuration feature of molecule plays an important role in modulating the π-conjugated delocalized degree. The X-ray crystallography further revealed the significant effect of hydrogen bonding on the planarity and aggregation mode of the molecular solid-state structure. The single-crystalline field effect transistor (FET) devices were fabricated and both compounds exhibit excellent FET performance with mobility over 0.8 cm²V⁻¹s⁻¹. All the results suggest that it would be an effective method to balance the solubility and electrical properties of organic π-conjugated compounds through regulating the molecular configuration by introduction of the hydrogen bonds.

为了探索氢键对有机半导体的影响，合成了四个具有扭曲构型的新型苯并[ b ]噻吩-苯并[ b ]呋喃类似物，并在常规溶剂中表现出良好的溶解性。光学，电化学特性和DFT模拟计算表明，分子的构型特征在调节π共轭离域度中起重要作用。X射线晶体学进一步揭示了氢键对分子固态结构的平面性和聚集模式的显着影响。制作了单晶场效应晶体管（FET）器件，这两种化合物均显示出出色的FET性能，迁移率超过0.8 cm ² V ^-1s ^-1。所有结果表明，通过引入氢键调节分子构型来平衡有机π-共轭化合物的溶解度和电性能将是一种有效的方法。