Synthesis and Optical, Electrochemical, and Electron-Transporting Properties of Silicon-Bridged Bithiophenes
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Abstract
A series of bithiophene derivatives bearing an intramolecular monosilanylene or disilanylene bridge between the β,β‘-positions were synthesized, and their properties were investigated. UV spectral and cyclic voltammetric analyses of the silicon-bridged bithiophenes indicated that they have lower lying LUMOs, relative to those for bithiophene and methylene bridged bithiophenes, probably due to σ*−π* interaction between the silicon atom(s) and bithiophene π-orbitals, in good agreement with the results of theoretical calculations using simplified model compounds based on RHF/6-31G. The silicon-bridged bithiophenes exhibit high electron-transporting properties, and triple-layer-type electroluminescent (EL) devices, using the silicon-bridged bithiophenes, tris(8-quinolinolato)aluminum(III) complex (Alq), and N,N‘-diphenyl-N,N‘-di-m-tolylbiphenyl-4,4‘-diamine (TPD) as the electron-transporting, emitting, and hole-transporting layers, respectively, emitted strong EL.
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