Synthesis, photophysical and electrochemical properties of symmetric silicon-linked diphenyl 1,3,4-oxadizole derivatives

Abstract

A series of novel, symmetric, silicon-linked, V-shaped, organic fluorescent compounds 1a–c with an electron-deficient 1,3,4-oxadizoles unit and a diphenyl moiety were successfully synthesized. We show that the Si atom possesses a special V-shaped structure that weakens π–π stacking resulting in aggregation-induced emission. This new type of compound may show tunable light emission in solution and in a solid-state thin film. Theoretical calculations were used to analyze the frontier molecular orbitals of the two compounds. The HOMO and LUMO energy levels of the studied compounds range from −1.55 to −1.78 eV and from −5.70 to −6.15 eV, indicating that they will function well as electron transport materials.