Synthesis, characterization and solid-state emission properties of arylsilyl-substituted pyrene derivatives

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• 作者：Qiuhong Wang ; Hui Liu ; Hua Lu ; Zheng Xu ; Guoqiao Lai ; Zhifang Li ; John Mack ; Zhen Shen
• 关键词：Pyrene dyes ; MCD spectroscopy ; Fluorescence ; TD-DFT calculations ; Pigments ; Solid-state emission
• 刊名：Dyes and Pigments
• 出版年：December, 2013
• 年：2013
• 卷：99
• 期：3
• 页码：771-778
• 全文大小：1590 K

文摘

Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (桅_F) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (桅_F聽=聽0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.