二萘并噻咯的合成及性能 |
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作者单位: | 1. Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University, Tianjin 300072, P. R. China;2. Tianjin Kingsrial S & T Company, Limited, Tianjin 300384, P. R. China |
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基金项目: | the National Natural Science Foundation of China(21102099) |
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摘 要: |
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关 键 词: | 二萘并噻咯 偶联反应 锂化反应 循环伏安 热重分析 有机电致发光器件 |
收稿时间: | 2016-12-21 |
Synthesis and Properties of a Series of Dinaphthosiloles |
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Authors: | Hong-Mei QU Ze-Peng CHONG Xu CHEN Yi-Can MEN Hai-Jiao SHEN |
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Institution: | 1. Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University, Tianjin 300072, P. R. China;2. Tianjin Kingsrial S & T Company, Limited, Tianjin 300384, P. R. China |
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Abstract: | Siloles constitute an important emerging class of photoluminescent materials. A series of compounds consisting of silole cores and fused naphthalene were synthesized and characterized:6, 6-dimethyl-1, 2, 3, 4, 8, 9, 10, 11-octapropyl-6H-dinaphtho2, 3-b:2', 3'-d]silole, 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-dimethyl-6H-dinaphtho2, 3-b:2', 3'-d]silole, 6, 6-diphenyl-1, 2, 3, 4, 8, 9, 10, 11-octapropyl-6H-dinaphtho2, 3-b:2', 3'-d]silole, and 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-diphenyl-6H-dinaphtho2, 3-b:2', 3'-d]silole. These dinaphthalene-fused siloles were synthesized from diiodonaphthalene, which was prepared by a direct coupling method. Subsequent reaction in the presence of n-butyllithium yielded 3, 3'-diiodo-2, 2'-binaphthalene. Direct substitution of two chloride ions from Ph2SiCl2 or Me2SiCl2 with 3, 3'-dilithio-2, 2'-binaphthalene then yielded the multi-substituted silole. Nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry were used to characterize the structures of the siloles. Their optical and electronic properties were investigated using ultraviolet-visible absorption spectroscopy, photoluminescence spectroscopy, cyclic voltammetry, and density functional theory calculations. The dinaphthalene-fused siloles exhibited similar absorption and emission peaks. Their deep highest occupied molecular orbital level at approximately -5.5 eV indicated that they were chemically stable. Differential scanning calorimetry and thermogravimetric analysis indicated that the siloles were stable up to 309℃. A multilayer electroluminescent device was fabricated using 1, 2, 3, 4, 8, 9, 10, 11-octabutyl-6, 6-dimethyl-6H-dinaphtho2, 3-b:2', 3'-d]silole as a light-emitting layer. The resulting device produced bright blue emission, indicating that these siloles may be suitable materials in organic light-emitting devices. |
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Keywords: | Dinaphthosilole Coupling reaction Lithiation reaction Cyclic voltammetry Thermogravimetric analysis Organic electroluminescent device |
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