Synthesis and Characteristics of 1,1-Dialkyl-2,5-diethynyl-3,4-diphenylsiloles
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초록
1,1-Dialkyl-2,5-diethynyl-3,4-diphenyl siloles 3a-c were synthesized in moderate yields as white solids through the desilylation reactions of 1,1-dialkyl-2,5-bis(trimethylsilylethynyl)-3,4-diphenylsiloles 2a-c. These materials were prepared from 1,1-dialkyl-2,5-dibromo-3,4-diphenylsiloles 1a-c. All the prepared structures of silole derivatives were characterized using 1H, 13C, 29Si NMR, FT-IR, UV-vis spectral data, and thermal stabilities using TGA. The synthesized siloles 2a-c and 3a-c were consistent with the structures proposed in the reaction scheme and were also studied with DFT calculations. The maximum absorption wavelengths of 2a-c and 3a-c were measured at 324~393 nm, which might be attributed to the chromophores of silolene-ethynylene originating from 2,5-bis(trimethylsilylethynyl) or -diethynyl-3,4-diphenylsiloles within the backbone of siloles prepared. 2a-c and 3a-c were stable up to 100℃ with less than 2% weight loss.
Abstract
1,1-Dialkyl-2,5-diethynyl-3,4-diphenyl siloles 3a-c were synthesized in moderate yields as white solids through the desilylation reactions of 1,1-dialkyl-2,5-bis(trimethylsilylethynyl)-3,4-diphenylsiloles 2a-c. These materials were prepared from 1,1-dialkyl-2,5-dibromo-3,4-diphenylsiloles 1a-c. All the prepared structures of silole derivatives were characterized using 1H, 13C, 29Si NMR, FT-IR, UV-vis spectral data, and thermal stabilities using TGA. The synthesized siloles 2a-c and 3a-c were consistent with the structures proposed in the reaction scheme and were also studied with DFT calculations. The maximum absorption wavelengths of 2a-c and 3a-c were measured at 324~393 nm, which might be attributed to the chromophores of silolene-ethynylene originating from 2,5-bis(trimethylsilylethynyl) or -diethynyl-3,4-diphenylsiloles within the backbone of siloles prepared. 2a-c and 3a-c were stable up to 100℃ with less than 2% weight loss.
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