TDDFT study on the photophysical properties of coumarinyl chalcones and sensing mechanism of a derived fluorescent probe for hydrogen sulfide

Xue, Yun-Shan; Liu, Yunping; Wang, Guirong; An, L.; Teng, Yangxin; Chen, Mohan; Xie, Yuxin; Zhang, Ling

doi:10.1016/j.saa.2020.118263

Cited by 21 publications

(8 citation statements)

References 81 publications

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“…[83] The reason behind the fluorescence quenching in sensing application for coumarin-based molecules also has been addressed by theoretical calculation. [84] Very recently, a detail review on small coumarin-based molecules for fluorescence sensing has been published by Lin et. al.…”

Section: Coumarin Dyes As Fluorescence Sensormentioning

confidence: 99%

An Insight of Molecular Twisting of Coumarin Dyes

Debnath

Ghosh

2020

ChemistrySelect

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This article highlights the recent understanding of twisted intramolecular charge transfer state (TICT) of coumarin dyes on TiO 2 and Au NP surface. The natural origin of coumarin dye in several plants makes it attractive to solar cell and fluorescence sensing applications. Two different classes of D-π-A coumarin dyes, having cyano-acrylic acid as acceptor and 7-amino moiety as a donor, have been chosen: one of them, having 7-amino moiety in the ring, shows only intramolecular charge transfer (ICT) states in the excited state. While due to twisting of the free 7-amino moiety, the second class of coumarin shows both ICT and TICT states in their photo-excited states in the polar environment, in the form of a strong dual-fluorescence. On TiO 2 surface such coumarin dyes found to couple with carboxylic moiety, however on Au NP surface they bind with amino moiety. As a result, on TiO 2 surface, the 7-amino moiety is free to rotate, thus exhibiting TICT state which is a charge-separated state and leads to higher electron injection yield for the second class of coumarins. The applicability of such twisted conformers of coumarin molecules in the solar cell has been demonstrated. Furthermore, due to molecular coupling with the 7-amino moiety on Au NP surface, a restriction imposed on the molecular twisting of the free 7-amino group. This constrains the formation of the TICT state for the second class of coumarins on the Au NP surface. Such ICT-TICT fluorescence modulation character of the coumarin dyes may lead them to use for fluorescence sensing application, which is also demonstrated to detect specific ions and biomolecules. Thus the present review acmes very fundamental photophysical properties of coumarin dyes based on their molecular twisting on different solvents, semiconductors, and metal nanoparticles which have great consequences of real life applications.

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Section: Coumarin Dyes As Fluorescence Sensormentioning

confidence: 99%

An Insight of Molecular Twisting of Coumarin Dyes

Debnath

Ghosh

2020

ChemistrySelect

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“…According to our previous studies, [59,60,76] the s-cis conformers of coumarin-chalcone are more stable than the s-trans ones. Thus, in this study, only the s-cis conformer was considered for the probe CCH.…”

Section: Ground-and Excited-state Geometriesmentioning

confidence: 93%

“…In addition, the applicability of the PBE0 functional for the studied systems has also been confirmed by previous studies on coumarin-chalcone hybrids. [59,60,66] In order to simulate the experimental environment, solvent effects were included using the polarizable continuum model (PCM) [67,68] in all calculations. It is well known that the conventional TDDFT method may suffer severe failure when dealing with CT excited states.…”

Section: Methodsmentioning

confidence: 99%

“…[42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57] To the best of our knowledge, no theoretical study has been reported on the photophysical properties and biothiols recognition mechanism for the studied probe CCH. In continuation of our research on the optical properties of chalcone derivates [58][59][60] and the development of novel fluorescent probes, [61,62] in this study, we aim to investigate the photophysical properties and cysteine recognition reaction of CCH to clarify the excitedstate nature and the sensing mechanism for biothiols. To this end, the electronic structure and transition character of the ground and excited states were explored, and the thermodynamic and kinetic properties of the thiols (Cys)-Michael addition reaction were studied.…”

mentioning

confidence: 99%

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Photophysical properties and sensing mechanism of fluorescent coumarin–chalcone hybrid for biothiols: A theoretical study

Zhang

Chen

et al. 2022

J of Physical Organic Chem

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The photophysical properties and sensing mechanism of a novel coumarinchalcone hybrid fluorescent probe (CCH) for biothiols were investigated by density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods. The theoretical calculations well reproduced the experimental spectra and clarified the experimental observed fluorescence "on-off" switching. Potential energy surface (PES) results revealed that the excited-state intramolecular proton transfer (ESIPT) process is thermodynamically and kinetically viable for CCH, with the keto form more stable than the enol form.ESIPT process and the significant changes of the orbital energies should be responsible for the red fluorescence of CCH. The results revealed that the lowest lying transition of probe CCH corresponds to electronic transition between HOMO and LUMO with charge transfer (CT) character. The addition of cysteine to CCH breaks the conjugation and the intramolecular CT. A nonclassical photoinduced electron transfer (PET) process should contribute to the fluorescence quenching of CCH-Cys. Thermodynamic and kinetic calculations on the recognition reaction predicted a moderate Gibbs free energy barrier, which proves the possibility of the Michael addition reaction and induces the rapid response of the probe CCH for cysteine.biothiols, coumarin-chalcone hybrids, DFT/TDDFT, photophysical property, sensing mechanism | INTRODUCTIONBiothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), are indispensable functional molecules in biological system, which play vital roles in many physiological processes, such as protein synthesis and metabolism. [1,2] The endogenous concentrations of thiols reflect the functional state of the corresponding enzymes and proteins, and their abnormal levels are associated with many diseases including cancer and Alzheimer's disease. [1][2][3][4] Therefore, it is of great value to detect and sense biothiols.Ling Zhang and Mohan Chen contributed equally.

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“…The Gaussian 09 programs suite was adopted for calculations. Using the density functional theory (DFT) method, geometry optimizations were performed with the hybrid functional PBE0 and 6-311G (d,p) basis set, which has been successfully applied in previous studies. , Vibrational frequency was determined at an equivalent level to characterize the stationary point as minima points . The vertical transition energies of the absorption were determined by the TD-PBE0/6-311G (d,p) approach.…”

Section: Methodsmentioning

confidence: 99%

Dual-Responsive Ratiometric Fluorescent Probe for Hypochlorite and Peroxynitrite Detection and Imaging In Vitro and In Vivo

Huang

Yan

et al. 2022

Anal. Chem.

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Hypochlorite (ClO − ) and peroxynitrite (ONOO − ) are two crucial highly reactive oxygen/nitrogen species, which interplay with each other, and are implicated in numerous pathophysiological processes. The simultaneous detection of ClO − and ONOO − is immensely significant in evaluating the occurrence and progress of related diseases. Herein, a dualresponsive ratiometric fluorescent probe PTZ-H for the separate and simultaneous detection of ClO − and ONOO − was designed and synthesized. In this probe, the phenothiazine-based coumarin moiety was chosen as the ClO − responsive fluorescent fragment, and the precursor of 2-(benzo[d]thiazol-2-yl)aniline was employed as the sensor for ONOO − . The PTZ-H emitted red fluorescence (640 nm) can switch to green (520 nm) and turn on blue fluorescence (450 nm) in response to ClO − and ONOO − , respectively. This allowed the specific recognition and ratiometric quantification of ClO − and ONOO − with the detection limits of 17 and 21 nM, respectively. Notably, confocal laser scanning microscopy revealed that the PTZ-H probe could target-specifically image ClO − and ONOO − in living RAW 264.7 cells, zebrafish, and tissues with distinct fluorescence signals. With the aid of this single fluorescent probe, the endogenous accumulation of ClO − and ONOO − in inflammatory RAW 264.7 cells and zebrafish can be monitored through two distinct emission channels with fast responses. Moreover, the large fluorescence signal interval, high selectivity, and good biocompatibility may enable its application in deciphering the distribution and correlation of ClO − and ONOO − engaged in biological activity.

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TDDFT study on the photophysical properties of coumarinyl chalcones and sensing mechanism of a derived fluorescent probe for hydrogen sulfide

Cited by 21 publications

References 81 publications

An Insight of Molecular Twisting of Coumarin Dyes

An Insight of Molecular Twisting of Coumarin Dyes

Photophysical properties and sensing mechanism of fluorescent coumarin–chalcone hybrid for biothiols: A theoretical study

Dual-Responsive Ratiometric Fluorescent Probe for Hypochlorite and Peroxynitrite Detection and Imaging In Vitro and In Vivo

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