Syntheses and Characteristics of Oligo[(4,4-disubstituted- 2,6-dithieno[3,2-b:2′,3′-d]silolene)-alt-(disubstituted silylene)]s
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Co-oligomerizations of 2,6-dilithio-4,4-diisopropyl- or -diphenyl-dithieno[3,2-b:2′,3′-d]siloles, which were prepared in situ via n-butyllithium treatment of 2,6-dibromo-4,4-diisopropyl- or -diphenyl-dithieno[3,2-b:2′,3′-d]siloles (V or VI), with dichlorodiisopropylsilane or dichlorodiphenylsilane yielded the novel oligomers oligo[(4,4-disubstituted-2,6- dithieno[3,2-b:2′,3′-d]silolene)-alt-(disubstituted silylene)]s VII-X as blue-greenish viscous liquids. These oligomers were characterized using several spectroscopic methods, such as 1H and 13C nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy, photophysical properties, and thermal stabilities, along with density functional theory (DFT) calculations. The absorption spectra of VII, VIII, and X, in particular, revealed partial delocalization over the oligomer backbones in comparison with those of the monomers V and VI, which was consistent with the highest occupied molecular orbital-lowest unoccupied molecular orbital energy trends calculated using DFT. VII-X were generally stable up to 150°C, with the less than 4% loss of the original mass.
Abstract
Co-oligomerizations of 2,6-dilithio-4,4-diisopropyl- or -diphenyl-dithieno[3,2-b:2′,3′-d]siloles, which were prepared in situ via n-butyllithium treatment of 2,6-dibromo-4,4-diisopropyl- or -diphenyl-dithieno[3,2-b:2′,3′-d]siloles (V or VI), with dichlorodiisopropylsilane or dichlorodiphenylsilane yielded the novel oligomers oligo[(4,4-disubstituted-2,6- dithieno[3,2-b:2′,3′-d]silolene)-alt-(disubstituted silylene)]s VII-X as blue-greenish viscous liquids. These oligomers were characterized using several spectroscopic methods, such as 1H and 13C nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy, photophysical properties, and thermal stabilities, along with density functional theory (DFT) calculations. The absorption spectra of VII, VIII, and X, in particular, revealed partial delocalization over the oligomer backbones in comparison with those of the monomers V and VI, which was consistent with the highest occupied molecular orbital-lowest unoccupied molecular orbital energy trends calculated using DFT. VII-X were generally stable up to 150°C, with the less than 4% loss of the original mass.
참고문헌 (18)
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