Synthesis, photophysical and electrochemical properties of symmetric silicon-linked diphenyl 1, 3, 4-oxadizole derivatives. Issue 18 (6th May 2015)

• Record Type: Journal Article
• Authors: Li, Dongfeng; Huang, Zhuo; Shang, Xiaohong; Xia, Yan; Zhang, Yuandong; Li, Min; Li, Bao; Hou, Ruibin
• Is Part Of: Tetrahedron. Volume 71:Issue 18(2015)
• Page Start: 2680
• Page End: 2685
• Publication Date: 2015-05-06
• Subjects: 1, 3, 4-Oxadizoles -- Electron-transporting materials -- Theoretical calculation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.03.039
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A series of novel, symmetric, silicon-linked, V-shaped, organic fluorescent compounds1a –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. Graphical abstract: