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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2879 - 2887

DOI: https://doi.org/10.6023/cjoc202005005

Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes

  • Liu Bingkang ,
  • Zhang Yanli ,
  • Chen Yu ,
  • Liu Xuguang ,
  • Zhang Lei
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  • a Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion & Tianjin Key Laboratory of Drug Targeting and Bioimaging, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384;
    b School of Science, Tianjin Chengjian University, Tianjin 300384;
    c Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2020-05-03

  Revised date: 2020-06-05

  Online published: 2020-06-19

Supported by

Project supported by the National Natural Science Foundation of China (No. 21502140), the Natural Science Foundation of Tianjin City (No. 17JCZDJC37700), and the Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules (No. K2015-10).

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Abstract

Repalcement of C=C bond with an isoeletronic and isosturctural B—N bond is an effective way to tune the photophyscial properties of polycylic aromatic hydrocarbons (PAHs), which have become the hot topic in the filed of optoelectronics. There are relatively smalll number of the non-planar BN-PAHs exsited, compared to the large number of planar BN-PAHs being synthesized. In this paper, the synthesis and properties of two series of non-planar BN[4]helicenes are discribed. The synthesis is quite straightforward by sequence of Suzuki cross coupling reaction, electrophilic borylation and nuleophilic substitution reactions. All of the target BN-[4]helicenes were characterized by 1H NMR, 13C NMR and 11B NMR. One of the BN-[4]helicene was also unmbigiously confired by X-ray crystal analysis, which showed the typical helically twisted geometries. Futhermore, the BC4N ring in the BN[4]helicene exhibited weak aromaticites, wihch were quantitified by experimental and theorectical calculations. Furthermore, both of the two series of BN[4]helicene showed significant redshift of their absorption spectra and slightly blueshift emission spectra comparing to the all-carbon [4]helicene analogue. Also, good fluorescence quantum yields range from 0.42 to 0.70 were obtained for the two series of BN[4]helicenes.

Key words： arenes/aromatics; boron/nitrogen heterocycle; helicene; boron

Cite this article

Liu Bingkang , Zhang Yanli , Chen Yu , Liu Xuguang , Zhang Lei . Synthesis, Characterization and Photophysical Properties of BN-[4]helicenes[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2879 -2887 . DOI: 10.6023/cjoc202005005

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