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Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

机译：通过多环芳烃的O环剪裁颜色

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摘要

The synthesis of O-doped polyaromatic hydrocarbons in which two polycyclic aromatic hydrocarbon sub units are bridged through one or two O atoms has been achieved. This includes high-yield ring-closure key steps that, depending on the reaction conditions, result in the formation of furanyl or pyranopyranyl linkages through intramolecular C-O bond formation. Comprehensive photophysical measurements in solution showed that these compounds have exceptionally high emission yields and tunable absorption properties throughout the UV/Vis spectral region. Electrochemical investigations showed that in all cases O annulation increases the electron-donor capabilities by raising the HOMO energy level, whereas the LUMO energy level is less affected. Moreover, third-order nonlinear optical (NLO) measurements on solutions or thin films containing the dyes showed very good values of the second hyperpolarizability. Importantly, poly(methyl methacrylate) films containing the pyranopyranyl derivatives exhibited weak linear absorption and NLO absorption compared to the nonlinearity and NLO refraction, respectively, and thus revealed them to be exceptional organic materials for photonic devices.
机译：已经实现了邻掺杂多芳族烃的合成，其中桥接两个多环芳烃亚单元通过一个或两个原子桥接。这包括根据反应条件的高屈服圈闭合键步骤，导致通过分子内C-O键形成形成呋喃基或吡喃吡喃基键。溶液中综合的光药测量表明，这些化合物在整个UV / VIS光谱区域中具有异常高的发光产率和可调谐吸收性能。电化学研究表明，在所有情况下，通过提高同性能水平，o附图增加了电子供体能力，而娄能较小的情况较小。此外，含有染料的溶液或薄膜上的三阶非线性光学（NLO）测量显示出非常好的第二超极化值。重要的是，含有吡喃吡喃基衍生物的聚（甲基丙烯酸甲酯）薄膜分别表现出与非线性和NLO折射相比的弱线性吸收和NLO吸收，因此显示它们是光子器件的特殊有机材料。

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  • 来源
    《Chemistry: A European journal》 |2017年第10期|共16页
  • 作者

    Tanja Mileti?; Andrea Fermi; Ioannis Orfanos; Aggelos Avramopoulos; Federica De Leo; Nicola Demitri; Giacomo Bergamini; Paola Ceroni; Manthos G. Papadopoulos; Stelios Couris; Davide Bonifazi;

  • 作者单位

    Department of Chemical and Pharmaceutical Sciences INSTM UdR Trieste University of Trieste Piazzale Europa 1 34127 Trieste (Italy);

    School of Chemistry Cardiff University Park Place CF10 3AT Cardiff (UK);

    Department of Physics University of Patras 26504 Patras (Greece);

    Institute of Biology Medicinal Chemistry and Biotechnology National Hellenic Research Foundation 48 Vas. Constantinou Avenue Athens 11635 (Greece);

    Department of Chemistry University of Namur (UNamur) 61 Rue de Bruxelles Namur 5000 (Belgium);

    Elettra-Sincrotrone Trieste S.S. 14 Km 163.5 in Area Science Park 34149 Basovizza-Trieste (Italy);

    Department of Chemistry "Giacomo Ciamician" University of Bologna Via Selmi 2 40126 Bologna (Italy);

    Department of Chemistry "Giacomo Ciamician" University of Bologna Via Selmi 2 40126 Bologna (Italy);

    Institute of Biology Medicinal Chemistry and Biotechnology National Hellenic Research Foundation 48 Vas. Constantinou Avenue Athens 11635 (Greece);

    Department of Physics University of Patras 26504 Patras (Greece);

    Department of Chemical and Pharmaceutical Sciences INSTM UdR Trieste University of Trieste Piazzale Europa 1 34127 Trieste (Italy);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    annulation; chromophores; doping; nonlinear optics; polycyclic aromatic hydrocarbons;

    机译：环状;发色;掺杂;非线性光学;多环芳烃;

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