A substituent-dependent deep-blue pyrene-based chemosensor for trace nitroaniline sensing

• Published in: Materials chemistry frontiers 2023-08, Vol.7 (16), p.3365-3372
• Main Authors: Li, Hua-Long, Cao, Jing-Yi, Yu, Ze-Dong, Yang, Guang, Xue, Zeng-Min, Wang, Chuan-Zeng, Zhao, Wen-Xuan, Zhao, Yi, Redshaw, Carl, Yamato, Takehiko
• Format: Article
• Language: English
• Subjects: Chemical sensors; Chemoreceptors; Density functional theory; Electron transfer; Photoluminescence; Pi-electrons
• ISSN: 2052-1537; 2052-1537
• DOI: 10.1039/d3qm00342f

Nitroaniline ( NA ) is a kind of high toxicity and pathogenic amine derivative, and the trace monitoring of nitroaniline has become an urgent problem in terms of both the environment and security. Herein, two K-region multiple substituted pyrene-based luminogens with reasonable photoluminescence efficiency and blue emission (408-430 nm) have been synthesized and characterized. Their photophysical properties were carefully investigated in solution and in the solid state by experimental and density functional theory (DFT) methods. It is worth mentioning that both of these π-electron rich and extended π-conjugated materials were used for the detection of electron deficient nitroaromatics ( NACs ) based on a photo-induced electron transfer (PET) mechanism, and a sensitive response towards NA , especially for p -NA with a limit of detection (LOD) as low as 8.58 × 10 −9 M, was observed, with a fluorescence quenching efficiency up to 99.5%. These research results provided a low-cost and simple strategy for trace nitroaniline sensing. Two K-region multiple substituted pyrene-based luminogens were found to exhibit a sensitive response towards p -NA with a limit of detection as low as 8.58 × 10 −9 M.