Methyl position affect the fluorescence performance of HBT derivatives for the detection of hypochlorite under alkaline condition

Long Yu; Ruoxuan Guo; Yaru Yuan; Pengchen Su; Xin Li; Yuejie Ai; Mingtai Sun; Xiangke Wang; Dejian Huang; Suhua Wang

doi:10.1016/j.saa.2022.121583

Methyl position affect the fluorescence performance of HBT derivatives for the detection of hypochlorite under alkaline condition

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Nov 15:281:121583. doi: 10.1016/j.saa.2022.121583. Epub 2022 Jul 1.

Authors

Long Yu¹, Ruoxuan Guo², Yaru Yuan², Pengchen Su¹, Xin Li³, Yuejie Ai², Mingtai Sun⁴, Xiangke Wang², Dejian Huang⁵, Suhua Wang⁶

Affiliations

¹ MOE Key Laboratory of Resources and Environmental System Optimization, College of Environmental Science and Engineering, North China Electric Power University, Beijing, 102206, P R China; Guangdong Provincial Key Laboratory of Petrochemical Pollution Process and Control, School of Environmental Science and Engineering, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000, P R China.
² MOE Key Laboratory of Resources and Environmental System Optimization, College of Environmental Science and Engineering, North China Electric Power University, Beijing, 102206, P R China.
³ Guangdong Provincial Key Laboratory of Petrochemical Pollution Process and Control, School of Environmental Science and Engineering, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000, P R China.
⁴ Guangdong Provincial Key Laboratory of Petrochemical Pollution Process and Control, School of Environmental Science and Engineering, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000, P R China. Electronic address: mtsun@gdupt.edu.cn.
⁵ Department of Food Science and Technology, National University of Singapore, 3 Science Drive 2, 117542, Singapore.
⁶ MOE Key Laboratory of Resources and Environmental System Optimization, College of Environmental Science and Engineering, North China Electric Power University, Beijing, 102206, P R China; Guangdong Provincial Key Laboratory of Petrochemical Pollution Process and Control, School of Environmental Science and Engineering, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000, P R China. Electronic address: wangsuhua@ncepu.edu.cn.

PMID: 35797952
DOI: 10.1016/j.saa.2022.121583

Abstract

Five fluorescent derivatives of hydroxyphenyl-benzothiazole (HBT) with different methyl positions at the hydroxyphenyl group were synthesized with good yield. Their reactivity and fluorescent response to hypochlorite were carefully studied. It was found that the HBT derivatives with meta-methyl (3-HBT or 5-HBT) showed the highest reactivity to hypochlorite under basic conditions, accompanied by the most efficient fluorescence quenching, whereas HBT derivatives with ortho or para methyl exhibited the least reactivity to hypochlorite. The LUMO and HOMO of 3-HBT were further verified to explain the fluorescence behavior by density functional theory (DFT) calculation. The excellent selectivity of 3-HBT toward hypochlorite against other reactive oxygen species (ROS) was also evaluated under the same conditions. The compounds emit bright green fluorescence in a solid-state, which is convenient for designing sensing devices for hypochlorite in water samples. Thus, the HBT derivatives with meta methyl (3-HBT) were successfully applied to fabricate paper sensors for the quantification of hypochlorite in tap water. Hence, the fluorescent 3-HBT exhibits great promise as a selective and sensitive hypochlorite probe in chemical and biological applications.

Keywords: Alkali environment detection; Fluorescent sensor; Hypochlorite; Methyl; Solid fluorescence.

MeSH terms

Benzothiazoles / chemistry
Fluorescent Dyes* / chemistry
Hypochlorous Acid* / chemistry
Spectrometry, Fluorescence
Water / chemistry

Substances

Benzothiazoles
Fluorescent Dyes
Water
Hypochlorous Acid