A theoretical investigation about the excited state behavior for 2‐(6'‐hydroxy‐2'‐pyridyl)benzimidazole: The water‐assisted excited state proton transfer process

Tong, Yuping; Fu, Jing; Ma, Jing

doi:10.1002/jccs.201700446

Cited by 5 publications

(1 citation statement)

References 70 publications

(94 reference statements)

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“…As aforementioned, the addition of water into MeOH solution of NTBD enhances the aggregation of the compound with a predominant formation of (offset) “card pack” aggregates. Furthermore, it is also known that such a solvent may facilitate tautomerization processes via so-called water-assisted proton transfers both in ground and excited states, as well as in aggregated structures [ 58 , 59 , 60 ]. All these facts support the hypothesis that both tautomers contribute to the emission signal for NTBD in the mixed MeOH/H 2 O solution, with the keto* species formed as a locally excited state (due to a non-negligible population of such an isomer in the ground state) or due to efficient ESIPT processes.…”

Section: Resultsmentioning

confidence: 99%

Cooperativity of ESPT and Aggregation-Induced Emission Effects—An Experimental and Theoretical Analysis of a 1,3,4-Thiadiazole Derivative

Budziak-Wieczorek,

Kaczmarczyk,

Rząd

et al. 2024

IJMS

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4-[5-(Naphthalen-1-ylmethyl)-1,3,4-thiadiazol-2-yl]benzene-1,3-diol (NTBD) was extensively studied through stationary UV–vis absorption and fluorescence measurements in various solvents and solvent mixtures and by first-principles quantum chemical calculations. It was observed that while in polar solvents (e.g., methanol) only a single emission band emerged; the analyzed 1,3,4-thiadiazole derivative was capable of producing dual fluorescence signals in low polarity solvents (e.g., n-hexane) and certain solvent mixtures (e.g., methanol/water). As clearly follows from the experimental spectroscopic studies and theoretical modeling, the specific emission characteristic of NTBD is triggered by the effect of enol → keto excited-state intramolecular proton transfer (ESIPT) that in the case of solvent mixture is reinforced by aggregation of thiadiazole molecules. Specifically, the restriction of intramolecular rotation (RIR) due to environmental hindrance suppresses the formation of non-emissive twisted intramolecular charge transfer (TICT) excited keto* states. As a result, this particular thiadiazole derivative is capable of simultaneously producing both ESIPT and aggregation-induced emission (AIE).

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Section: Resultsmentioning

confidence: 99%

Cooperativity of ESPT and Aggregation-Induced Emission Effects—An Experimental and Theoretical Analysis of a 1,3,4-Thiadiazole Derivative

Budziak-Wieczorek,

Kaczmarczyk,

Rząd

et al. 2024

IJMS

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Revealing and comparing different excited‐state intramolecular proton transfer processes for 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐propenone and 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐3‐hydroxy‐propenon

Gao

Song

Yang

et al. 2020

J Chinese Chemical Soc

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Two novel 2′‐hydroxychalcone derivatives (i.e., M1 and M2) are explored in this work. We mainly focus on investigating the effects of photoexcitation on hydrogen bonds and on the excited‐state intramolecular proton transfer (ESIPT) process. On the basis of calculations of electrostatic potential surface and intramolecular interactions, we verify the formation of hydrogen bond O1H2···O3 in both S0 and S1 states. Exploring the ultraviolet–visible spectra in the liquid phase, our simulated results reappear in the experimental phenomenon. Analyzing molecular geometry and infrared stretching vibrational spectra, we confirm O1H2···O3 is strengthened for both M1 and M2 in the S1 state. We further confirm that charge redistribution facilitates ESIPT tendency. Constructing potential energy curves, we find the ultrafast ESIPT behavior for M1, which is because of the deficiency of side hydroxyl moiety comparing with M2. This work makes a reasonable affiliation of the ESIPT mechanism for M1 and M2. We wish this paper could facilitate understanding these two novel systems and promote their applications.

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Solvent‐polarity‐dependent excited‐state behaviors for 2‐(2‐hydroxyphenyl) benzothiazole‐5‐(9H‐carbazol‐9‐yl)phenol fluorophore: A theoretical study

Cao

Dong

2022

J of Physical Organic Chem

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In this work, we mainly focus on elaborating the effects of solvent polarity on excited state interactions and intramolecular proton transfer (ESIPT) behavior for the novel dye 2‐(2‐hydroxyphenyl) benzothiazole‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz). Six aprotic solvents with different polarities are considered. Via comparing geometrical parameters, infrared (IR) vibrational spectra, and atomic charge distributions, we confirm that the hydrogen bond of HBT‐Cz is enhanced in S1 state. The enhancement of hydrogen bonding with low polarity is particularly important. Via exploring molecular orbitals, we find that intramolecular charge transfer happens and charge redistribution facilitates ESIPT reaction. Results show that low solvent polarity is more conducive to ESIPT process for HBT‐Cz. In order to clarify detailed reaction mechanism, we construct potential energy curves and determine that the ESIPT process of HBT‐Cz fluorophores could be controlled by solvent polarity. We not only elucidate the excited state behavior of HBT‐Cz systems but also present the polarity‐dependent ESIPT mechanism for HBT‐Cz fluorophore.

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A theoretical investigation about the excited state behavior for 2‐(6'‐hydroxy‐2'‐pyridyl)benzimidazole: The water‐assisted excited state proton transfer process

Cited by 5 publications

References 70 publications

Cooperativity of ESPT and Aggregation-Induced Emission Effects—An Experimental and Theoretical Analysis of a 1,3,4-Thiadiazole Derivative

Cooperativity of ESPT and Aggregation-Induced Emission Effects—An Experimental and Theoretical Analysis of a 1,3,4-Thiadiazole Derivative

Revealing and comparing different excited‐state intramolecular proton transfer processes for 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐propenone and 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐3‐hydroxy‐propenon

Solvent‐polarity‐dependent excited‐state behaviors for 2‐(2‐hydroxyphenyl) benzothiazole‐5‐(9H‐carbazol‐9‐yl)phenol fluorophore: A theoretical study

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