Synthesis and Characteristics of 5,5-Diphenyl-5H-dibenzo[b,d]silole
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The synthesis of 5,5-diphenyl-5H-dibenzo[b,d]silole (3) resulted in a satisfactory yield of 60.7%, yielding a white solid. This was achieved by reacting the prepared 2,2-dibromobiphenyl (2) in the yield of 78.7%, obtained through the reaction of 2,2-dibromobenzene (1) as the starting material, with n-butyllithium and followed by dichlorodiphenylsilane in tetrahydrofuran solvent. Compounds 2 and 3 were characterized using 1H, 13C, 29Si NMR, FT-IR, and UV-vis spectral data. Additionally, their thermal stability was assessed using thermogravimetric analysis. The structural conformity of compounds 2 and 3 with the proposed reaction scheme 1 was confirmed, and further validation was performed through DFT calculations. The prepared compounds 2 and 3 exhibited exceptional stability, with a weight loss not exceeding 1% up to 100℃ under a nitrogen atmosphere. The electrochemical properties of compound 3 were evaluated, revealing a C-rate performance of 1,016 mAhg-1 at 0.2 A/g and a long cycling performance of 1,909 mAhg-1 with a Coulombic efficiency of 90.8% after 500 cycles.
Abstract
The synthesis of 5,5-diphenyl-5H-dibenzo[b,d]silole (3) resulted in a satisfactory yield of 60.7%, yielding a white solid. This was achieved by reacting the prepared 2,2-dibromobiphenyl (2) in the yield of 78.7%, obtained through the reaction of 2,2-dibromobenzene (1) as the starting material, with n-butyllithium and followed by dichlorodiphenylsilane in tetrahydrofuran solvent. Compounds 2 and 3 were characterized using 1H, 13C, 29Si NMR, FT-IR, and UV-vis spectral data. Additionally, their thermal stability was assessed using thermogravimetric analysis. The structural conformity of compounds 2 and 3 with the proposed reaction scheme 1 was confirmed, and further validation was performed through DFT calculations. The prepared compounds 2 and 3 exhibited exceptional stability, with a weight loss not exceeding 1% up to 100℃ under a nitrogen atmosphere. The electrochemical properties of compound 3 were evaluated, revealing a C-rate performance of 1,016 mAhg-1 at 0.2 A/g and a long cycling performance of 1,909 mAhg-1 with a Coulombic efficiency of 90.8% after 500 cycles.
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