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Revisiting Unsubstituted Ullazine: Concise Synthesis, Single Crystal X-Ray Structure and Photophysical Properties
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  • Tian Liu,
  • Yuanhui Wang,
  • Ruijun Jiang,
  • Rui Gong,
  • Lei Zhang,
  • Xuguang Liu,
  • Jun Deng
Tian Liu
Chongqing University
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Yuanhui Wang
Tianjin University of Technology
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Ruijun Jiang
Tianjin University of Technology
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Rui Gong
Chongqing University
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Lei Zhang
Tianjin Chengjian University
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Xuguang Liu
Tianjin University of Technology

Corresponding Author:liuxuguang123@163.com

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Jun Deng
Chongqing University
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Abstract

We have developed an efficient synthetic route of parental ullazine in three steps from commercially available synthons with overall yield of 53%. The single crystal X-ray structure of parental ullazine was studied in detail. Parental ullazine core can be functionalized either by late-stage Vilsmeier-Haack formylation/condensation sequence or by C-N cross-coupling with a pre-installed bromine. Pre-liminary results show that the condensation of CHO-substituted ullazine (U-CHO) gave a novel imidazole substituted ullazine. The brominated ullazine (U-Br) can undergo Buchwald-Hartwig cross-coupling smoothly, resulting a carbazole substituted ullazine. In ad-dition, parental ullazine showed redshifted absorption and emission spectra as compared to its isoelectronic isomer pyrene, and no excimer formation in higher concentration.