Understanding solvent polarity dependent excited state behavior and ESIPT mechanism for 2-benzo[b]thiphen-3-yl-3-hydroxy-6-methoxy-chroman-4-one compound

Xiao, Shusen; Lou, Zhangrong; Ji, Debin; Zhao, Jinfeng

doi:10.1016/j.cplett.2021.138409

Cited by 35 publications

(13 citation statements)

References 62 publications

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“…To further investigate the photo-induced PT behavior of BHI compound in different solvents, we used potential energy curve sweeps to study the changes in system energy as a function of one or more geometric variables. [67][68][69][70][71] Based on the theoretical DFT/TDDFT method, the detailed dynamic process of the BHI compound could be revealed in S 0 and S 1 states. In the step of 0.05 Å, potential energy curves have been constructed with increasing O-H bond distance from 0.90 to 2.25 Å (seen in Figure 4).…”

Section: Potential Energy Curve Analysismentioning

confidence: 99%

“…That is to say, under the circumstances, the forward PT reaction in the S 0 state should be inhibited. [66][67][68][69][70][71] In the S 1 state, however, the potential barrier changes to be small. And after crossing the peak of potential curves, the potential energy decreases with the increasement of O-H bond distance in three solvents.…”

Section: Potential Energy Curve Analysismentioning

confidence: 99%

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Solvent polarity‐dependent ESIPT behavior for 5‐(benzothiazole‐2‐yl)‐4‐hydroxyisophthalaldehyde fluorophore: A theoretical study

Guan

Tang

et al. 2022

J Chinese Chemical Soc

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In view of the potential applications of 5‐(benzothiazole‐2‐yl)‐4‐hydroxyisophthalaldehyde (BHI) in the rapid identification of cyanide, the mechanism of excited‐state intramolecular proton transfer (ESIPT) of BHI has been studied in this work. By exploring the geometric parameters of hydrogen bonding in aprotic solvents with different polarities, infrared (IR) vibrational spectroscopy 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 polar solvents is particularly important. In light‐induced excitation, by comparing the energy gaps of the leading molecular orbitals and the charge recombination around the proton acceptor and donor in aprotic solvents of different polarities, it is further predicted that polar solvents can promote the ESIPT process of BHI. In order to clarify the detailed ESIPT mechanism, we constructed the potential energy curves, searched for the transition state (TS) form, and determined the ESIPT mechanism for BHI fluorophore. Herein, we not only elucidated the excited‐state behavior of BHI, but also proposed a mechanism for regulating ESIPT by solvent polarity.

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Section: Potential Energy Curve Analysismentioning

confidence: 99%

Section: Potential Energy Curve Analysismentioning

confidence: 99%

Solvent polarity‐dependent ESIPT behavior for 5‐(benzothiazole‐2‐yl)‐4‐hydroxyisophthalaldehyde fluorophore: A theoretical study

Guan

Tang

et al. 2022

J Chinese Chemical Soc

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“…Based on the tunable luminescent properties, a series of scientific research fields have been involved in ESIPT behaviors, such as fluorescent sensors, white light LEDs, cell imagines, and so forth. [14][15][16][17][18] In fact, due to the photo-excitation behavior, charge reorganization results in more acidic donors and more basic proton receptors, and this leads to changes in electronic densities that trigger ESIPT behavior. Given the multiple potential applications involved in ESIPT, regulatory ESIPT response has become the fours of research in recent years.…”

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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“…[9,10] Over the years, there are numerous studies by theoretical as well as experimental methods to explore the hydrogen bonding interaction. [11][12][13][14][15][16][17][18][19][20][21] In general, hydrogen bonding can be defined as the interaction between a proton donor and proton acceptor atom (such as X-HÁÁÁY), and both proton donor and acceptor atoms are usually electronegative atoms. [22] For example, the pyridyl nitrogen, carbonyl oxygen, or azole-nitrogen group act as the acceptor of the proton, whereas the amino, hydroxyl, and occasionally pyrrolic groups serve as proton donor groups.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the dehydrogenation mechanism of dihydrogen‐bonded phenol‐borane‐dimethylamine complex in the ground and excited states

Cao

et al. 2022

J of Physical Organic Chem

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In this work, the density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods were adopted to explore the dehydrogenation mechanism of phenol-borane-dimethylamine (phenol-BDMA) complex in ground (S 0 ) and excited (S 1 ) states. The analysis of the geometric parameters and infrared (IR) vibrational spectra indicate that the dihydrogen bond H 1 ÁÁÁH 2 is significantly strengthened in S 1 state and the dehydrogenation process may occur along the dihydrogen bond H 1 ÁÁÁH 2 . Upon photo-excitation, the electronic density of phenol-BDMA complex is redistributed and the redistribution of the electronic density can provide driving force for the dehydrogenation process in S 1 state. The potential energy curves reveal that the dehydrogenation

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Understanding solvent polarity dependent excited state behavior and ESIPT mechanism for 2-benzo[b]thiphen-3-yl-3-hydroxy-6-methoxy-chroman-4-one compound

Cited by 35 publications

References 62 publications

Solvent polarity‐dependent ESIPT behavior for 5‐(benzothiazole‐2‐yl)‐4‐hydroxyisophthalaldehyde fluorophore: A theoretical study

Solvent polarity‐dependent ESIPT behavior for 5‐(benzothiazole‐2‐yl)‐4‐hydroxyisophthalaldehyde fluorophore: A theoretical study

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

Unveiling the dehydrogenation mechanism of dihydrogen‐bonded phenol‐borane‐dimethylamine complex in the ground and excited states

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