Akinobu Naka, R. Fukuda, Yoshifumi Jahana
Oct 1, 2013
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Influential Citations
5
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Journal
Journal of Organometallic Chemistry
Abstract
Abstract The H-shaped molecule, 5,5′-bis{[bis(5′- tert -butyldimethylsilyl)-2,2′-(bithiophen-5-yl)]methylsilyl}-2,2′-bithiophene ( 3 ) was prepared by the reaction of 5′-( tert -butyldimethylsilyl)-5-lithio-2,2′-bithiophene with 2-bromo-5-(dichloromethylsilyl)thiophene, followed by treatment of the resulting product (5-bromothiophen-2-yl)bis[5′-( tert -butyldimethylsilyl)-2,2′-bithiophen-5-yl](methyl)silane ( 1 ) with compound ( 2 ), obtained by the reaction of the lithiated derivative of 1 with 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, in the presence of dichlorobis(triphenylphosphine)palladium, as light yellow solids. Compound 3 showed absorption maximum ( λ max ) at 336 nm with a molar absorption coefficient ( e ) of 113,000 M −1 cm −1 in dioxane. The fluorescence spectrum of 3 excited at 336 nm in dioxane displayed the emission maxima at 377 and 387 nm, with the fluorescence quantum yield of 48%. We also carried out theoretical treatment of compound 3 to elucidate the geometrical and electronic structure, using the Gaussian 03 program package, with the 6-31G and 6-31G(d) basis sets.