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首页> 外文期刊>New Journal of Chemistry >Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone beta-diketonate complexes
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Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone beta-diketonate complexes

机译：新型和高荧光二氟rOOs黄酮β-二酮肽复合物的合成，光药和电化学性能

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摘要

Difluoroboron beta-diketonates complexes are highly luminescent with extensive properties such as their fluorescence both in solution and in solid state and their high molar extinction coefficients. Due to their rich optical properties, these compounds have been studied for their applications in organic electronics such as in self-assembly and applications in biosensors, bio-imaging and optoelectronic devices. The easy and fast synthesis of difluoroboron beta-diketonate (BF(2)dbm) complexes makes their applications even more attractive. Although many different types of difluoroboron beta-diketonates complexes have been studied, the cyclic flavanone analogues of these compounds have never been reported in the literature. Therefore, the present work aims to synthesize difluouroboron flavanone beta-diketonate complexes, study their photophysical and electrochemical properties and assess their suitability for applications in optoelectronic devices. The synthesis was based on a Baker-Venkataraman reaction which initially provided substituted diketones, which were subsequently reacted with aldehydes to afford the proposed flavanones. The complexation was achieved by reacting flavanones and BF3 center dot Et2O and in total 9 novel compounds were obtained. A representative difluoroboron flavanone complex was subjected to single crystal X-ray diffraction to unequivocally confirm the chemical structure. A stability study indicated only partial degradation of these compounds over a few days in a protic solvent at elevated temperatures. Photophysical studies revealed that the substituent groups and the solvent media significantly influence the electrochemical and photophysical properties of the final compounds, especially the molar absorption coefficient, fluorescence quantum yields, and the band gap. Moreover, the compounds exhibited a single excited-state lifetime in all studied solvents. Computational studies were employed to evaluate ground and excited state properties and carry out DFT and TDDFT level analysis. These studies clarify the role of each state in the experimental absorption spectra as well as the effect of the solvent.
机译：DifluoroBoronβ-二氧酯复合物具有高度发光，具有广泛的性质，例如溶液中的荧光和固态和它们的高摩尔消光系数。由于其富光学性质，已经研究了这些化合物，用于其在有机电子产品中的应用，例如在自组装和生物传感器，生物成像和光电器件中的应用。轻松快速地合成DifluoroBoronβ-二酮（BF（2）DBM）配合物使其应用更具吸引力。虽然已经研究了许多不同类型的二氟硼醇β-二酮复合物，但这些化合物的环状黄烷酮类似物从未在文献中报道。因此，本作工作旨在合成Difluouroboron Flavanoneβ-二酮复合物，研究它们的光学和电化学性能，并评估它们在光电器件中的应用的适用性。合成基于贝克 - venkataraman反应，其最初提供取代的二酮，随后与醛反应，得到提出的黄烷酮。通过使黄烷酮和BF3中心点Et 2 O反应来实现络合，得到总共9种新化合物。对代表性的二氟硼酮络合物进行单晶X射线衍射，以明确证实化学结构。稳定性研究表明，在升高的温度下的质子溶剂中仅在几天内部分降解这些化合物。光药研究表明，取代基和溶剂介质显着影响最终化合物的电化学和光学性质，尤其是摩尔吸收系数，荧光量子产量和带隙。此外，化合物在所有研究的溶剂中表现出单一的激发态寿命。使用计算研究来评估地面和激发的状态性质，进行DFT和TDDFT水平分析。这些研究阐明了每个状态在实验吸收光谱中的作用以及溶剂的作用。

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  • 来源
    《New Journal of Chemistry》 |2020年第34期|共17页
  • 作者

    Ariza Paez Elida Betania; Curcio Sergio; Neme Natalia P.; Matos Matheus J. S.; Correa Rodrigo S.; Pereira Fabio Junio; Hilario Flaviane Francisco; Cazati Thiago; Taylor Jason Guy;

  • 作者单位

    Univ Fed Ouro Preto ICEB Chem Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Phys Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Phys Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Phys Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Chem Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Chem Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Chem Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Phys Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

    Univ Fed Ouro Preto ICEB Chem Dept Campus Univ Morro Cruzeiro BR-35400000 Ouro Preto MG Brazil;

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