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

Liu, Xiumin; Qi, Yutai; Pu, Shenhan; Wang, Yi; Gao, Zhuo

doi:10.1039/d1ra02511b

Cited by 28 publications

(17 citation statements)

References 55 publications

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“…[116] This section will discuss QD-based strategies for biological H 2 S sensing (summarized in Table 3). Fluorescent-based QD probes for monitoring and imaging analytes of interest primarily rely on FRET [124] or photoinduced electron transfer (PET) [125] mechanisms. Sensitivity in these cases depends on the distance between the donor-acceptor or charge transfer chromophore-quencher pairs, respectively.…”

Section: Quantum Dot (Qd)-based Probesmentioning

confidence: 99%

Synthetic nanoprobes for biological hydrogen sulfide detection and imaging

Zhou

Mazur

Fan

et al. 2022

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Hydrogen sulfide (H2S) is a gaseous molecule involved in multiple biological and physiological processes, including various diseases such as cancer and neurodegenerative disorders. This has led to the development of various analytical methods to monitor H2S in biological settings. Among these, fluorescence‐based assays, specifically organic small‐molecule probes, have been thoroughly utilized. They offer good sensitivity and specificity as sensors, and noninvasive detection with high spatiotemporal resolution in in vitro and in vivo imaging. Despite attempts to decrease the rate of photobleaching and enhance the photostability of these dyes, they are still limited by low survival time and complex reagent pretreatment. Fortunately, nanotechnology has been applied to develop effective, highly sensitive, and specific fluorescent nanoprobes. Specifically, nanomaterial‐based H2S probes have emerged as promising candidates for real‐time detection and imaging. In contrast to their organic molecule‐based counterparts, they offer higher versatility in imaging modes due to their unique optical properties, improved photostability and solubility within physiological fluids, as well as easily modifiable surfaces and tuneable structures for improved specificity. Recently, many nanomaterial‐based probes, ranging from inorganic nanoparticles to self‐assembled nanocomposites, have been developed. These have, for the most part, achieved sensitive and specific endogenous H2S detection and in vivo imaging. In this review, we evaluate five different nanomaterials currently being researched to detect and image endogenous H2S within the last 5 years. Furthermore, analytical methods associated with the various signal outputs, current challenges in H2S nanoprobe design, and possible future research interests are outlined and discussed.

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Section: Quantum Dot (Qd)-based Probesmentioning

confidence: 99%

Synthetic nanoprobes for biological hydrogen sulfide detection and imaging

Zhou

Mazur

Fan

et al. 2022

VIEW

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“…[3,4] So far, the generation of excited hydrogen bonds has become the focus of researchers, because the excited hydrogen bonds can affect the fluorescence sensing mechanism of compounds. [5][6][7][8][9][10][11] Thiazole compounds containing hydroxyl are a typical excited state intramolecular proton transfer (ESIPT) system with intramolecular hydrogen bonds. [12][13][14][15][16] Thiazole ring is an important type of five-membered aromatic heterocyclic ring.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study on excited state intramolecular proton transfer mechanism of thiazole complex in different kinds of solvents

Liu

Wang

et al. 2022

J of Physical Organic Chem

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The excited state intramolecular proton transfer (ESIPT) processes of 3-(benzo [d]-thiazol-2-yl)-2-hydroxy-5-methoxybenzaldehyde (BTHMB) in four kinds of solvents were studied using density functional theory (DFT) and timedependent DFT (TDDFT) method. As the solvent dielectric constant decreases, the strength of hydrogen bonds (H-bonds) in the excited state decreases. After photoexciation, the electron density rearrangement could be affected by the solvents, while the degree of charge transfer and the hydrogen bond interaction in the excited state became lower as the solvent dielectric constant decreased. The potential energy curves displayed the complete process of ESIPT, indicating that the ESIPT process of BTHMB was affected by the solvent polarity. When the solvent dielectric constant decreased, the tendency of proton transfer followed the trend: acetonitrile (ACN) > dichloromethane (DCM) > chloroform (CHCl 3 ) > 1,4-dioxane (DOX). Therefore, the ESIPT process was affected by the solvent polarity and became more difficult to occur as the solvent dielectric constant decreased. K E Y W O R D Sexcited state intramolecular proton transfer, hydrogen bond, potential energy curves, solvent polarity

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“…As far as we know, much attention has been directed toward the excited state intramolecular and intermolecular proton transfer (ESIPT) of hydrogen-bonded molecular systems from both theoretical and experimental aspects in recent years. [1][2][3][4][5][6][7][8][9] Particularly, due to the unique orientation and saturation properties, multiple hydrogen bonding interactions have played important roles in chemical, biological, and physical fields. [10][11][12][13] Over half a century of research history, it has been concluded the ESIPT reaction belongs to a kind of simple chemical behavior readily assessable for both quantum simulations and accurate measurement analyses.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation into the deciphering effects of atomic electronegativity on 2‐hydroxy‐phenyl‐tafamidis: A time‐dependent density functional theory study

Zhang

Yuan

2022

J Chinese Chemical Soc

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In light of the potential probe applications of 2‐hydroxy‐phenyl‐tafamidis (2HPT) and its derivatives with different atomic electronegativity (2HPT‐O, 2HPT‐S, and 2HPT‐Se), the mechanisms of excited state intramolecular proton transfer (ESIPT) of 2HPT derivatives have been investigated in this work. Via probing into the geometric parameters of hydrogen bond O‐H···N, infrared vibrational spectroscopy, and bond critical point values, we can confirm that hydrogen bonding is enhanced in the first excited state (S1). It is worth mentioning that the enhancement of hydrogen bonding in the S1 state by low atomic electronegativity 2HPT‐Se is particularly important. In light‐induced excitation, by comparing the changed behaviors of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) orbitals, it could be found that photo‐induced charge transfer happens in excited molecules, and charge redistribution facilitates ESIPT reaction. Particularly, the low atomic electronegativity could promote the ESIPT process for 2HPT system. In order to clarify the detailed ESIPT mechanism, we construct the potential energy curves, search for the transition state form, and determine the ESIPT mechanism for 2HPT fluorophores. In this work, we not only elucidated the excited state behavior of 2HPT systems but also proposed a novel mechanism for regulating ESIPT by atomic electronegativity.

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

Cited by 28 publications

References 55 publications

Synthetic nanoprobes for biological hydrogen sulfide detection and imaging

Synthetic nanoprobes for biological hydrogen sulfide detection and imaging

Theoretical study on excited state intramolecular proton transfer mechanism of thiazole complex in different kinds of solvents

Theoretical investigation into the deciphering effects of atomic electronegativity on 2‐hydroxy‐phenyl‐tafamidis: A time‐dependent density functional theory study

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