Toward New Materials for Organic Electroluminescent Devices: Synthesis, Structures, and Properties of a Series of 2, 5-Diaryl-3,4-diphenylsiloles

✍ Scribed by Shigehiro Yamaguchi; Tomonori Endo; Manabu Uchida; Takenori Izumizawa; Kenji Furukawa; Kohei Tamao

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 249 KB
• Volume: 6
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(20000502)6:9<1683::aid-chem1683>3.0.co;2-m

✦ Synopsis

A series of 2,5-diaryl-3,4-diphenylsiloles, with various mono-substituted phenyl groups, extended p-conjugated groups, and heteroaryl groups as aryl groups at the 2,5-positions, has been prepared by a one-pot synthesis from bis(phenylethynyl)silanes based on the intramolecular reductive cyclization followed by the palladium-catalyzed cross-coupling with aryl halides. Crystal structures and chemical reactivities toward the alkaline desilylation reactions have been studied on the 2,5-bis(p-mono-substituted phenyl)silole derivatives to elucidate the effects of the p-substituents. The UV-visible absorption and fluorescence spectra, and cyclic voltammetry of the 2,5-diarylsiloles have been systematically evaluated. Their photophysical properties as well as their electronic structures significantly depend on the nature of the 2,5-aryl groups.