Hydrogen-bond activated ESIPT in naphthalimide-based fluorescent probe for sensing volatile amines

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 281; p. 121567
• Main Authors: Tang, Xinxue, Zhu, Xuguang, Xu, Huilong, Sun, Hao, Han, Xiang'en, Li, Qun, Zhou, Binbin, Ni, Zhonghai
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.11.2022
• Subjects: Expanded conjugation; Food freshness; H-ESIPT; Naphthylamide derivatives; Volatile amines detection; Volatile amines detection; Food freshness; Naphthylamide derivatives; Expanded conjugation; H-ESIPT
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2022.121567

We report a recyclable visual packaging bag for volatile amines detections based on the naphthylamide derivative N-S and its positive PL characteristics. Specifically, handmade test strips based on compound N-S have been applied to fish freshness labeling, and the cyclic fumigation experiment shows a restorable PL effect and efficiency of the probe N-S. [Display omitted] •N-S is a newly synthesized compound with exhibited competitive amines detection limits and allows for visual detection of biogenic amines from spoiled fish.•The visual detection of volatile amines is reusable after protonation.•N-S exhibited approximately 53 nm wavelength red-shift from bright green to yellow fluorescence stimulated by the H-ESIPT process.•A visual probe N-S for volatile amines shows good stability and recycling potential. Amines levels present important indicative value in food safety and human health. Although they are involved in some normal physiological responses of the organism, their overproduction or intake may cause pathological responses. Herein, we report a recyclable visual packaging bag for volatile amines detections based on the naphthylamide derivative N-S and its positive PL characteristics. Specifically, handmade test strips based on compound N-S have been applied to fish freshness labeling, and the cyclic fumigation experiment shows its restorable PL effect and efficiency. The possible PL transfer mechanism of naphthylamide derivative N-S is uncovered by the density functional theory (DFT) calculation and titration mass spectrometer and 1H NMR. This work expands a conjugation in a molecule by hydrogen-bond activated ESIPT (H-ESIPT) and provides a portable detection method for volatile amines detection.