Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study

Yang, Dapeng; Yang, Guang; Zhao, Jinfeng; Song, Ning; Zheng, Rui; Wang, Yusheng

doi:10.1002/poc.3729

Cited by 11 publications

(10 citation statements)

References 72 publications

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“…Compounds that undergo excited state intramolecular proton transfer (ESIPT), discovered first by Weller, have attracted attention due to their applications in green fluorescent protein, bioimaging, organic light‐emitting diodes, fluorescent chemosensors, and photophysical studies . In general, the molecules with the ESIPT properties exist in the enol form at the ground state, stabilized by a heterocyclic ring, which consists of the intramolecular hydrogen bond (IMHB) between a hydroxyl group and a neighboring proton acceptor.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Yin

Shi

2018

J of Physical Organic Chem

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We theoretically investigate the excited state behaviors of the novel fluorophore tetraphenylethene-2-(2′-hydroxyphenyl)benzothiazole (TPE-HBT), which was designed based on the intersection of TPE and HBT, using density functional theory and time-dependent density functional theory methods. Compared with previous experimental results about fluorescence peaks, our calculated results are in good agreement with experimental data, which further confirms that the theoretical level we used is reasonable. Furthermore, our results confirm that the excited state intramolecular proton transfer (ESIPT) process happens upon photoexcitation, which is distinctly monitored by the infrared spectra and the potential energy curves. In addition, the calculation of highest occupied molecular orbital and lowest unoccupied molecular orbital reveals that the electron density change of proton acceptor because of the intramolecular charge transfer (ICT) process in the S 1 state induces the ESIPT. Moreover, the transition density matrix is worked out to facilitate deeper insight into the ESIPT coupled ICT process. It is hoped that the present work not only elaborates the ESIPT coupled ICT phenomenon and corresponding mechanisms for the TPE-HBT but also may be helpful to design and develop new materials and applications involved in TPE-HBT systems in future.KEYWORDS excited state intramolecular proton transfer, intramolecular charge transfer, potential energy curves, time-dependent density functional theory

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Section: Introductionmentioning

confidence: 99%

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Yin

Shi

2018

J of Physical Organic Chem

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“…To the best of our knowledge, theoretical IR vibrational spectra should be another reasonable manner to explore excited state hydrogen bonding interactions . Therefore, in this present work, we also perform the simulations of the IR vibrational spectra (shown in Figure ).…”

Section: Resultsmentioning

confidence: 99%

A time‐dependent density functional theory study on the excited state behavior of a novel T₂(OH)B molecule

Jia

Song

Yang

et al. 2019

J Chinese Chemical Soc

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A novel pH-sensitive fluorescent probe T 2 (OH)B was selected to theoretically investigate its excited state hydrogen bonding effects and excited state intramolecular proton transfer (ESIPT) process. First, it was verified that one intramolecular hydrogen bond is formed spontaneously in T 2 (OH)B itself. Given the geometrical changes, we further confirm that the hydrogen bond should be strengthened in the first excited state. When it comes to the photoexcitation process, we present the charge redistribution around hydrogen bonding moieties facilitate the ESIPT tendency. The increased electronic densities around acceptor promote the attraction of hydrogen protons. The potential energy barrier in the constructed potential energy curves reveals that the ESIPT process of the T 2 (OH)B system should be ultrafast.And comparing several nonpolar solvents, we deem solvent polarity plays little role in the ESIPT reaction. Furthermore, we also search the S 1 -state transition state structure along with the ESIPT path, based on which we simulate the intrinsic reaction coordinate path. We not only confirm the ESIPT mechanism presented in this work but also clarify the ultrafast excited state process and explain previous experiment. We sincerely hope that our theoretical work could guide novel applications based on the T 2 (OH)B system in future. K E Y W O R D Scharge distribution, ESIPT, intramolecular hydrogen bond, potential energy curve

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“…[ 17 ] Among these, solvent molecules play indispensable roles, which could combine with solutes to form complexes or set up bridges between hydrogen‐bonding acceptors and donors to promote the occurrence of hydrogen‐bond dynamics. [ 18‐23 ] Therefore, solvent effect should be fully considered in theoretical researches. [ 24‐25 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Sensing Mechanism of Excited‐State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide

et al. 2021

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Density-functional-theory/Time-dependent density-functional-theory | Hydrogen bonds | Fluorescent probes | Electron transfer | Dimethyl sulfoxide Excited-state hydrogen bond strongly affects the intramolecular charge conversion process, which is very suitable for the design and development of high-performance fluorescent probes. However, as one of the most common solvents or additives used in sensing, the role of dimethyl sulfoxide (DMSO) in the system of the excited-state hydrogen bond is seldom explored. As the goal of this research, we investigated the sensing mechanism of a CORM3-green fluorescent probe system for carbon monoxide releasing molecule (CORM-3) detection and tracking in vivo, through quantum chemistry calculations based on density-functional-theory (DFT)/ time-dependent density-functional-theory (TDDFT) methods. Based on the analysis of the solvent effect of DMSO by the reduced density gradient function and IR spectroscopy, we provided a new strategy to explain the fluorescence mechanism. Subsequently, we verified the result through the potential energy curve of Phthalimide (PTI, the reduced product of CORM3-green). The excited-state hydrogen bond between PTI and DMSO promotes radiation transition and leads to obvious difference in the photophysical properties of PTI and PTI-DMSO.

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Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study

Cited by 11 publications

References 72 publications

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

A time‐dependent density functional theory study on the excited state behavior of a novel T₂(OH)B molecule

Sensing Mechanism of Excited‐State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide

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Solvent controlling excited state proton transfer reaction in quinoline/isoquinoline‐pyrazole isomer QP‐I: A theoretical study

Cited by 11 publications

References 72 publications

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

Theoretical investigation on the excited state intramolecular proton coupled charge transfer phenomenon for a novel fluorophore

A time‐dependent density functional theory study on the excited state behavior of a novel T2(OH)B molecule

Sensing Mechanism of Excited‐State Intermolecular Hydrogen Bond for Phthalimide: Indispensable Role of Dimethyl Sulfoxide

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A time‐dependent density functional theory study on the excited state behavior of a novel T₂(OH)B molecule