An ESIPT-based fluorescent turn-on probe with isothiocyanate for detecting hydrogen sulfide in environmental and biological systems

Jae Kyong Kim; So Yeon Bong; Rackhyun Park; Junsoo Park; Doo Ok Jang

doi:10.1016/j.saa.2022.121333

An ESIPT-based fluorescent turn-on probe with isothiocyanate for detecting hydrogen sulfide in environmental and biological systems

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Oct 5:278:121333. doi: 10.1016/j.saa.2022.121333. Epub 2022 May 4.

Authors

Jae Kyong Kim¹, So Yeon Bong¹, Rackhyun Park², Junsoo Park², Doo Ok Jang³

Affiliations

¹ Department of Chemistry, Yonsei University, Wonju 26493, Republic of Korea.
² Division of Biological Science and Technology, Yonsei University, Wonju 26493, Republic of Korea.
³ Department of Chemistry, Yonsei University, Wonju 26493, Republic of Korea. Electronic address: dojang@yonsei.ac.kr.

PMID: 35537263
DOI: 10.1016/j.saa.2022.121333

Abstract

A probe with an isothiocyanate group was synthesized and evaluated for its H₂S sensing ability. Upon addition of H₂S, the probe exhibited ratiometric properties during absorption with a red-shift. The probe exhibited fluorescent off-on responses towards H₂S via the ESIPT process, due to the conversion of isocyanate into amine. UV-vis, fluorescence, and ¹H NMR spectroscopic analyses were performed to investigate the sensing mechanism. The probe has a large Stokes shift, short response time, and low detection limit. It can be used to estimate H₂S levels within the range of 0-36 nM. The practical applicability of the probe was demonstrated using water samples and living cells.

Keywords: ESIPT; Fluorescent; Hydrogen sulfide; Isothiocyanate; Steric effect.

MeSH terms

Fluorescent Dyes* / chemistry
HeLa Cells
Humans
Hydrogen Sulfide* / analysis
Isothiocyanates
Spectrometry, Fluorescence

Substances

Fluorescent Dyes
Isothiocyanates
Hydrogen Sulfide