对甲基苯硫酚功能化的螺-9,9′-氧杂蒽芴的设计合成及其光电性质

Design, synthesis and photoelectric properties of the p‑methylthiophenol functionalized spiro‑9,9′‑oxanthrene fluorene

  • 摘要: 以氧化亚铜为催化剂,采用对甲基苯硫酚对螺-9,9′-氧杂蒽芴(SFX)进行了功能化修饰,成功地制备了新型螺环化合物2,7-双(4-甲基苯硫酚基)-螺-9,9′-氧杂蒽芴(DMePhS-SFX)。通过高分辨质谱、氢谱和碳谱对其分子结构进行了详细表征。热重分析曲线结果表明,DMePhS-SFX在失重5%时热分解温度高达375 oC。紫外吸收与荧光光谱结果表明,该化合物在220~370 nm区域有着较强的吸收,其最大发射峰波长为379 nm。通过低温磷光光谱测得该化合物的三线态能级为2.51 eV,表明该化合物作为主体材料可用于制备红、绿色磷光器件。通过循环伏安法测得其最高占据轨道(HOMO)和最低未占轨道(LUMO)能级分别为-5.88 eV和-2.16 eV。

     

    Abstract: A novel spiro compound 2,7-di(4-methylthiophenol)-spiro-9,9'-oxanthrene fluorene (DMePhS-SFX) was successfully prepared by functionalizing spiro-9,9′-oxanthrene fluorene (SFX) with p-methylthiophenol using cuprous oxide as a catalyst. The molecular structure was detailedly characterized by high resolution mass spectrometry, hydrogen spectroscopy and carbon spectroscopy. The data of thermogravimetric analysis showed that the thermal decomposition temperature of DMePhS-SFX was as high as 375 oC with 5% weight loss. The UV absorption and fluorescence spectra showed that the compound had intense absorption ranging from 220 to 370 nm, and the wavelength of its maximum emission peak was around 379 nm. The triplet energy level of the compound was 2.51 eV that was calculated from the first emission peak of phosphoresce luminescence at low temperature, which indicated that the compound could be used as host material to prepare red and green phosphorescent devices. The highest occupied orbit (HOMO) and the lowest unoccupied orbit (LUMO) energy levels were -5.88 eV and -2.16 eV, respectively, which were obtained by cyclic voltammetry.

     

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