Issue 36, 2021, Issue in Progress

Sensing mechanism of a new fluorescent probe for hydrogen sulfide: photoinduced electron transfer and invalidity of excited-state intramolecular proton transfer

Abstract

It is of great significance for biological research to develop efficient detection methods of hydrogen sulfide (H2S). When DFAN reacts with H2S, 2,4-dinitrophenyl ether group acting as an electron acceptor generates a hydroxyl-substituted 2,4-dinitrophenyl ether group, resulting in the disappearance of photoinduced electron transfer (PET), and the new formed DFAH can be observed, while being accompanied by a significant fluorescence. In the present study, the PET sensing mechanism of probe DFAN and the excited state intramolecular proton transfer (ESIPT) process of DFAH have been explored in detail based on the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. Our theoretical results show that the fluorescence quenching of DFAN is caused by the PET mechanism, and the result of ESIPT mechanism is not due to the large Stokes shift fluorescence emission of DFAH. We also optimized the geometric structure of the transition state of DFAH. The frontier molecular orbitals and potential barrier show that the ESIPT process does not easy occur easily for DFAH. The enol structure of DFAH is more stable than that of the keto structure. The absence of the PET process resulted in the enol structure emitting strong fluorescence, which is consistent with the single fluorescence in the experiment. Above all, our calculations are sufficient to verify the sensing mechanism of H2S using DFAN.

Graphical abstract: Sensing mechanism of a new fluorescent probe for hydrogen sulfide: photoinduced electron transfer and invalidity of excited-state intramolecular proton transfer

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2021
Accepted
02 Jun 2021
First published
23 Jun 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 22214-22220

Sensing mechanism of a new fluorescent probe for hydrogen sulfide: photoinduced electron transfer and invalidity of excited-state intramolecular proton transfer

X. Liu, Y. Qi, S. Pu, Y. Wang and Z. Gao, RSC Adv., 2021, 11, 22214 DOI: 10.1039/D1RA02511B

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements