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DOI: 10.1055/a-2640-2440
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A Strongly Fluorescent Dye Featuring a Multiple N-doped Polycyclic Aromatic Hydrocarbon Skeleton

Peihao Chen
1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)
,
Xintong Wan
2   huyanglin, 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
3   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
4   Department of Chemistry, The University of Hong Kong, Hong Kong, China (Ringgold ID: RIN25809)
,
Kai Li
1   College of Materials Science and Engineering, Shenzhen University, Shenzhen, China (Ringgold ID: RIN47890)
› Author Affiliations
Supported by: National Natural Science Foundation of China 22271196,22322505
Supported by: Research Team
Supported by: Basic and Applied Basic Research Foundation of Guangdong Province 2023A1515030176
Supported by: Cultivation Program of Shenzhen University 2023DFT004
Supported by: Instrumental Analysis Center of Shenzhen University
› Further Information
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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%). Taken together the electrochemical and computational studies, its bipolar nature is suggested. The fluorescence sensing capability towards 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 towards various applications.



Publication History

Received: 24 April 2025

Accepted after revision: 19 June 2025

Accepted Manuscript online:
20 June 2025

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