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Synlett 2025; 36(18): 3083-3088
DOI: 10.1055/a-2640-2440
Letter

A Strongly Fluorescent Dye Featuring a Multiple N-doped Polycyclic Aromatic Hydrocarbon Skeleton

Autoren

  • Peihao Chen

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Xintong Wan

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Yi Zhang

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Xiaoyong Chang

    2   Department of Chemistry, Southern University of Science and Technology, Shenzhen, China (Ringgold ID: RIN255310)

  • Ping Ouyang

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Jinfan Xiong

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Yang Zou

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • He Liu

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

  • Gang Cheng

    3   Department of Chemistry, The University of Hong Kong, Pok Fu Lam, Hong Kong (Ringgold ID: RIN25809)

  • Kai Li

    1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)

Gefördert durch: National Natural Science Foundation of China 22271196,22322505
Gefördert durch: Research Team
Gefördert durch: Basic and Applied Basic Research Foundation of Guangdong Province 2023A1515030176
Gefördert durch: Cultivation Program of Shenzhen University 2023DFT004
Gefördert durch: Instrumental Analysis Center of Shenzhen University
Funding Information This work was supported by the National Natural Science Foundation of China (22322505 and 22271196), the Research Team Cultivation Program of Shenzhen University (2023DFT004), and Guangdong Basic and Applied Basic Research Foundation (2023A1515030176). We also thank Instrumental Analysis Center of Shenzhen University for analytical support.
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Graphical Abstract

Abstract

This study presents the synthesis and characterization of a highly fluorescent compound derived from 5,11-dihydroquinoxalino[2,3-b]quinoxaline (tBQQ), which incorporates both sp3 and sp2 nitrogen atoms into a polycyclic aromatic hydrocarbon skeleton. Starting from 3,6-di-tert-butyl-9H-carbazole, the target compound was obtained in moderate yield through a key condensation cyclization and subsequent oxidation reactions. The new compound exhibits excellent photophysical properties, including intense absorption and high photoluminescence quantum yield (96%). Taking together the electrochemical and computational studies, its bipolar nature is suggested. The fluorescence sensing capability toward acid was also revealed for tBQQ, attributable to the presence of sp2 N atoms. This study provides an unexplored skeleton for the design of strongly fluorescent dyes toward various applications.

Keywords

Fluorescence - N-Heterocycles - π-Conjugated system - Polycyclic aromatic hydrocarbon - Organic semiconductor

Supplementary Material



Publikationsverlauf

Eingereicht: 24. April 2025

Angenommen nach Revision: 19. Juni 2025

Accepted Manuscript online:
20. Juni 2025

Artikel online veröffentlicht:
31. Juli 2025

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