Synthesis, structure, aggregation-induced emission, self-assembly, and electron mobility of 2,5-bis(triphenylsilylethynyl)-3,4-diphenylsiloles.

2,5-Bis(triphenylsilylethynyl)-3,4-diphenylsiloles with different 1,1-substituents [XYSi(CPh)(2) (C-C≡C-SiPh(3))(2)] (Ph=phenyl) were synthesized in high yields by the Sonogashira coupling of 2,5-dibromo-3,4-diphenylsiloles with triphenylsilylacetylene, and two of these were characterized crystallographically. Crystal structures and theoretical calculations showed that the new silole molecules had higher conjugation than 2,5-diarylsiloles. They possessed low HOMO and LUMO energy levels due to the electron-withdrawing effect of the triphenylsilylethynyl groups.