Solvent effects on excited state intramolecular proton transfer mechanism in 4-(N,N-dimethylamino)-3-hydroxyflavone

Li-feng, Jia; Wang, Fang; Liu, Yufang

doi:10.1016/j.orgel.2018.03.030

Cited by 24 publications

(5 citation statements)

References 51 publications

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“…The ESIPT studies refer to a wide array of systems including proteins, metal complexes, DNA, polymers, microheterogeneous, and inclusion complexes. Up to now, multiple novel optoelectronic applications have been designed and developed via ESIPT properties, such as white light LEDs, fluorescent detectors, luminescent materials, laser dyes, and so forth. − …”

Section: Introductionmentioning

confidence: 99%

Solvent-Polarity-Dependent Excited-State Behavior and Thermally Active Delayed Fluorescence for Triquinolonobenzene

Zhao

Dong

Yang

et al. 2019

ACS Appl. Bio Mater.

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The triple hydrogen-bonded triquinolonobenzene (TQB) molecule is investigated for its excited-state dynamics and proton transfer (ESIPT) mechanism in different solvents in this work. Through insights into electrostatic potential surface (EPS), reduced density gradient, and isosurfaces of gradient, we confirm that three intramolecular hydrogen bonds are formed for the TQB molecule. Exploring geometrical parameters involved in hydrogen bonds, infrared (IR) vibrational spectra, and bond energy via atoms in molecules (AIM) analyses, it could be verified that hydrogen bonds are strengthened in the first (S1) excited state. Based on comparing the energy gaps among frontier molecular orbitals (MOs) in four aprotic solvents, we predict that the ESIPT reaction of TQB could be facilitated with the increase of solvent polarity. Comparing the relationship among all the stable configurations and simulating potential energy surfaces (PESs), we present that the ESIPT process of the TQB system could be controlled through solvent polarity. Given the thermally active delayed fluorescence (TADF) process of the ESIPT product in the S1 state via reverse intersystem crossing (RISC), we verify that polar solvents suppress the TADF process to some extent. We speculate that the moderate polar solvents can facilitate high efficiency photoluminescence for the TQB system, which endows the TQB system with a kind of compelling optoelectronic and biological material.

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Section: Introductionmentioning

confidence: 99%

Solvent-Polarity-Dependent Excited-State Behavior and Thermally Active Delayed Fluorescence for Triquinolonobenzene

Zhao

Dong

Yang

et al. 2019

ACS Appl. Bio Mater.

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“…The potential energy curve (PEC) can intuitively reveal the process of proton transfer at the S 0 state and S 1 state of compounds. [49][50][51][52] The potential energy curves of HPIP, 5 Br-HPIP, and 6 Br-HPIP in S 0 and S 1 states are described in Fig. 5.…”

Section: Potential Energy Curve and Mechanism Analysismentioning

confidence: 99%

Theoretical study on the relationship between the position of the substituent and the ESIPT fluorescence characteristic of HPIP*

Zhang

Han

et al. 2020

Chinese Phys. B

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The influences of the substituent base position on the excited state intramolecular proton transfer fluorescence properties were explored in 2-(2′-hydroxyphenyl)imidazo[1,2-a]-pyridine (HPIP) and HPIP’s derivatives (5′Br-HPIP and 6′Br-HPIP). And the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods were used to calculate the molecule structures. The calculated results showed that the influence of 5′Br-HPIP on the fluorescence intensity is stronger than that of 6′Br-HPIP. The fluorescence emission peak of 5′Br-HPIP occurred a blue shift compared with HPIP, and 6′Br-HPIP exhibited an opposite red shift. The change of the fluorescence emission peak was attributed to the decrease of the energy gap from 6′Br-HPIP to 5′Br-HPIP. Our work on the substituent position influence could be helpful to design and develop new materials.

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“…A low intensity band associated with its anionic form appears at longer wavelengths. From a theoretical point of view, the UV–vis spectrum and the ESIPT of 3-HF − and 3-HF-based chromophores − have been studied both in gas phase and in solution. Most of these studies have used TDDFT, although MNDO/AM1, , CIS, and CASPT2/CASSCF methods have also been applied.…”

Section: Introductionmentioning

confidence: 99%

A Theoretical Study of Solvent Effects on the Structure and UV–vis Spectroscopy of 3-Hydroxyflavone (3-HF) and Some Simplified Molecular Models

2023

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Solvent effects on the UV–vis spectra of 3-hydroxyflavone and other structurally related molecules (3-hydroxychromen-4-one, 3-hydroxy-4-pyrone, and 4-pyrone) have been studied by combining time-dependent density functional theory (TDDFT) and the polarizable continuum method (PCM). Among the first five excited states of the four considered molecules, electronic states of n → π* and π → π* nature appear. In general, the stability of the n → π* states decreases as the π space becomes larger in such a way that only for 4-pyrone and 3-hydroxy-4-pyrone are they the first excited states. In addition, they become less stabilized in ethanol solution than the ground state, and this causes blueshift transitions in solution. The opposite trend is found for the π → π* excited states. They are less energetic with the π-system size and when passing from gas phase to solution. The solvent shift also depends strongly on the size of the π systems and on the formation of an intramolecular hydrogen bond; thus, it decreases when going from 4-pyrone to 3-hydroxyflavone. The performance of the three versions (cLR, cLR2, and IBSF) of the specific-state PCM method in predicting transition energies are compared.

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Solvent effects on excited state intramolecular proton transfer mechanism in 4-(N,N-dimethylamino)-3-hydroxyflavone

Cited by 24 publications

References 51 publications

Solvent-Polarity-Dependent Excited-State Behavior and Thermally Active Delayed Fluorescence for Triquinolonobenzene

Solvent-Polarity-Dependent Excited-State Behavior and Thermally Active Delayed Fluorescence for Triquinolonobenzene

Theoretical study on the relationship between the position of the substituent and the ESIPT fluorescence characteristic of HPIP*

A Theoretical Study of Solvent Effects on the Structure and UV–vis Spectroscopy of 3-Hydroxyflavone (3-HF) and Some Simplified Molecular Models

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