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首页> 外文期刊>Organometallics >Synthesis and Photophysical Properties of Phenyleneethynylenes Containing a Combination of Two Main Group Element Moieties of B, Si, or P on the Side Chain
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Synthesis and Photophysical Properties of Phenyleneethynylenes Containing a Combination of Two Main Group Element Moieties of B, Si, or P on the Side Chain

机译：含苯基烯烯基的合成和光学性质，侧链两种主要群元素部分组合组合的组合

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摘要

X-shaped 1,4-phenyleneethynylenes containing a combination of two main group element moieties of B, Si, or P as part of the side chain have been synthesized. The halogen–lithium exchange of 2-bromo-5-dimethylphenylsilyl-1,4-bis(phenylethynyl)benzene followed by addition of fluorodimesitylborane or chlorodiphenylphosphine gave the “X-shaped” B/Si and Si/P, respectively. The P-containing molecule was oxidized to afford a P(═O) derivative. The B/PO moieties were introduced to the 1,4-phenyleneethynylene unit by 3 steps, i.e., the halogen–lithium exchange of 2,5-dibromo-1,4-bis(trimethylsilylethynyl)benzene followed by sequential addition of fluorodimesitylborane and chlorodiphenylphosphine oxide, desilylation, and the Sonogashira coupling with aryl iodides. Then, the reduction of the B/PO gave “X-shaped” B/P derivative. The absorption and fluorescence spectra of the “X-shaped” molecules showed the molecules have two-dimensional conjugation systems, i.e., the π-conjugation of the original π-conjugation backbone and p(B)π–π* conjugation of B, σ*?π* conjugation of Si, and n?π and σ*?π* conjugation of P, extended from the π-core. The highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy levels are significantly altered because of a lowering of the LUMO level due to p?π* conjugation for B and σ*?π* conjugation for Si and P compared with the parent phenyleneethynylene, which are also supported by density functional theory calculations.
机译：X形1,4-苯基乙烯烯基含有两个主要组元素部分的组合，如B，Si或P的一部分的一部分已经合成。 2-溴-5-二甲基苯基甲硅烷基-1,4-双（苯基乙炔基）苯的卤素 - 锂交换，然后加入氟代霉菌或氯共苯基膦，分别得到“X形”B / Si和Si / P。含p的分子被氧化以提供p（= O）衍生物。通过3步，即2,5-二溴-1,4-双（三甲基甲酰乙炔基）苯的卤素 - 锂交换，然后依次加入氟甲基氯烷和氯二苯基膦，将B / PO部分引入1,4-苯基乙烯单元。氧化物，脱甲硅烷化和Sonogashira与芳碘化物偶联。然后，减少B / PO给出“X形”的B / P衍生物。 “X形”分子的吸收和荧光光谱显示该分子具有二维缀合系统，即原始π-缀合骨架的π-缀合，P（b）π-π*缀合B，σ *π*π*缀合Si，N 2π和σ*π*π*缀合P，从π芯延伸。最高占用的分子轨道（HOMO） - 最无人居住的分子轨道（LUMO）能级是显着改变的，因为LUMO水平降低，由于B和σ*π*缀合而对Si和P相轭缀合用母苯基乙烯，其也被密度官能理论计算支持。

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  • 来源
    《Organometallics》 |2018年第3期|共9页
  • 作者

    Takanobu Sanji; Akemi Fuchigami; Masato Tanaka;

  • 作者单位

    Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta Midori-ku Yokohama 226-8503 Japan;

    Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta Midori-ku Yokohama 226-8503 Japan;

    Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta Midori-ku Yokohama 226-8503 Japan;

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  • 正文语种 eng
  • 中图分类 元素有机化合物;
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