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<p>Bis(dithiophene)-substituted benzo[1,2-<i>d</i>:4,3-<i>d</i>′]dithiazoles were synthesized by a photochemical cyclization of corresponding <i>N</i>,<i>N</i>′-(benzo[<i>c</i>][1,2,5]thiadiazole-4,7-diyl)- and <i>N</i>,<i>N</i>′-(2<i>H</i>-benzo[<i>d</i>][1,2,3]triazole-4,7-diyl)dithioamides in the presence of chloranil. The mechanism of this cyclization was analyzed. The influence of the structure of the central heterocycle on the electrochemical, electronic, and photophysical properties of the synthesized compounds was studied. Quantum yields for THF solutions of the luminophpores are in the range 0.16–0.62. An increase in the electron-withdrawing effects of the central heterocycle stabilizes the radical anion and reduces the reduction potential, E<sub>onset</sub><sup>red</sup>, and the width of the band gap.</p>

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Photophysical and electrochemical properties of bis(dithiophene)-substituted benzo[1,2-d:4,3-d′]dithiazoles

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • A. S. Kostyuchenko,
  • E. B. Uliankin,
  • T. Yu. Zheleznova,
  • A. L. Shatsauskas,
  • V. Yu. Shuvalov,
  • A. S. Fisyuk

摘要

Bis(dithiophene)-substituted benzo[1,2-d:4,3-d′]dithiazoles were synthesized by a photochemical cyclization of corresponding N,N′-(benzo[c][1,2,5]thiadiazole-4,7-diyl)- and N,N′-(2H-benzo[d][1,2,3]triazole-4,7-diyl)dithioamides in the presence of chloranil. The mechanism of this cyclization was analyzed. The influence of the structure of the central heterocycle on the electrochemical, electronic, and photophysical properties of the synthesized compounds was studied. Quantum yields for THF solutions of the luminophpores are in the range 0.16–0.62. An increase in the electron-withdrawing effects of the central heterocycle stabilizes the radical anion and reduces the reduction potential, Eonsetred, and the width of the band gap.