Benzophenoxazine-based colorimetric and fluorescent probe for highly sensitive detection of amines and food freshness

Hongjin Wang; Wenzhu Yin; Hui Ma; Xiaoyan He; Gui Yin; Wei Huang

doi:10.1016/j.saa.2023.123004

Benzophenoxazine-based colorimetric and fluorescent probe for highly sensitive detection of amines and food freshness

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Dec 5:302:123004. doi: 10.1016/j.saa.2023.123004. Epub 2023 Jun 11.

Authors

Hongjin Wang¹, Wenzhu Yin², Hui Ma³, Xiaoyan He⁴, Gui Yin⁵, Wei Huang⁶

Affiliations

¹ College of Chemistry and Environmental Science, Yili Normal University, Yining 835000, PR China; State Key Laboratory of Coordination Chemistry, State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China.
² Institute of Veterinary Immunology & Engineering, National Research Center of Engineering and Technology for Veterinary Biologicals, Jiangsu Academy of Agricultural Sciences, Nanjing 210014, PR China.
³ State Key Laboratory of Coordination Chemistry, State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China.
⁴ College of Chemistry and Environmental Science, Yili Normal University, Yining 835000, PR China.
⁵ College of Chemistry and Environmental Science, Yili Normal University, Yining 835000, PR China; State Key Laboratory of Coordination Chemistry, State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China. Electronic address: yingui@nju.edu.cn.
⁶ State Key Laboratory of Coordination Chemistry, State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, PR China; Shenzhen Research Institute of Nanjing University, Shenzhen 518057, PR China. Electronic address: whuang@nju.edu.cn.

PMID: 37348275
DOI: 10.1016/j.saa.2023.123004

Abstract

In this work, we reported a chromogenic and near infrared (NIR) region fluorogenic dual-channel probe NRB, which could visually detect gaseous amines with high sensitivity (eg. 50 and 17 ppt for methylamine (MeNH₂) via naked eyes and fluorescence spectrometer respectively). It exhibited a wide fluorescent emission band extending to the NIR region with a peak at 615 nm when stimulated by the MeNH₂ solution. The plausible sensing mechanism was proved by mass spectrometry, where the reaction process was based on a nucleophilic substitution between the probe and amines rather than the ester group hydrolysis. Furthermore, NRB was successfully applied to monitor the food freshness (seafood and meat food), because of its low cytotoxicity and excellent photophysical properties. It was worth mentioning that real time monitoring for food quality can be realized visually by using a 365 nm UV lamp. In addition, the probe was stable during the quality guarantee period for perishable packaged food. It was believed that the applied experiments have demonstrated the value of this probe in the practical applications for food safety.

Keywords: Amines detection; Benzophenoxazine-based compound; Colorimetric and NIR fluorescent sensor; Food freshness monitoring.

MeSH terms

Amines*
Colorimetry / methods
Fluorescent Dyes* / chemistry
Food Quality
Meat

Substances

Fluorescent Dyes
Amines