Tunable excited-state intramolecular proton transfer reactions with N H or O H as a proton donor: A theoretical investigation

Li, Yuanyuan; Wen, Keke; Feng, Songyan; Yuan, Huijuan; An, Beibei; Zhu, Qiuling; Guo, Xugeng; Zhang, Jinglai

doi:10.1016/j.saa.2017.06.019

Cited by 36 publications

(8 citation statements)

References 47 publications

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“…In other words, these changes about chemical bond distances and bond angles indicate that the dual hydrogen bonds (O1H2⋯N3 and O4H5⋯N6) of BDABE should be strengthened in the S 1 state . In addition, it is well known that the excited‐state hydrogen bonding interactions could also be revealed by theoretical IR vibrational spectra . Thus, we also simulated the IR vibrational spectra involved in hydrogen‐bonding moieties, which is shown in Figure .…”

Section: Resultsmentioning

confidence: 98%

Theoretical insights into excited‐state process for the novel 2,3‐bis[(4‐diethylamino‐2‐hydroxybenzylidene)amino]but‐2‐enedinitrile system

Zhang

Yang

et al. 2019

J Chinese Chemical Soc

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In this present work, we clarify the excited‐state intramolecular proton transfer (ESIPT) mechanism for 2,3‐bis[(4‐diethylamino‐2‐hydroxybenzylidene)amino]but‐2‐enedinitrile (BDABE) system. We present the fact that excited‐state single proton transfer can occur along with one hydrogen bond, even though BDABE form consists of two intramolecular hydrogen bonds. Based on the density functional theory and time‐dependent density functional theory methods, we theoretically investigate and elaborate the excited‐state intramolecular dual hydrogen‐bonding interactions. By simulating the electrostatic potential surface, we verify the formation of dual intramolecular hydrogen bonds for BDABE molecule in the S0 state. Furthermore, comparing the primary bond lengths and bond angles as well as the infrared vibrational spectra, we find that the double hydrogen bonds should be strengthened in the S1 state. When it comes to photoexcitation process, we discover the charge redistribution around hydrogen bonding moieties. The increased electronic density around proton acceptor plays the important roles in strengthening hydrogen bonds and in facilitating ESIPT reaction. In view of the possible ESIPT reaction paths (i.e., stepwise and synchronization double proton transfer) for BDABE molecule, we explored the S0‐state and S1‐state potential energy curves. This work explains experimental results and further clarifies the excited‐state behaviors for BDABE system.

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Section: Resultsmentioning

confidence: 98%

Theoretical insights into excited‐state process for the novel 2,3‐bis[(4‐diethylamino‐2‐hydroxybenzylidene)amino]but‐2‐enedinitrile system

Zhang

Yang

et al. 2019

J Chinese Chemical Soc

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“…A hydrogen-bonded strength was determined by the important distance parameters involving ESIntraPT and ESInterPT processes namely the covalent O-H bond of 3HF and a water molecule, the intraHB between proton donor and proton acceptor of 3HF, and the interHBs between 3HF and a water molecule for the case study of water assisted effect. The strength of all intraHB and interHBs was further confirmed by the red-shift values of the O-H stretching vibrational frequencies between the S 0 and S 1 states from the simulated IR spectra, together with the topology analysis at bond critical point (BCP) from quantum theory of atoms in molecules (QTAIM) performed by Multiwfn [68], which was employed in previous studies [69][70][71]. The electronic spectra and frontier MOs were also calculated.…”

Section: Quantum Chemical Calculationsmentioning

confidence: 91%

Effect of Water Microsolvation on the Excited-State Proton Transfer of 3-Hydroxyflavone Enclosed in γ-Cyclodextrin

et al. 2021

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The effect of microsolvation on excited-state proton transfer (ESPT) reaction of 3-hydroxyflavone (3HF) and its inclusion complex with γ-cyclodextrin (γ-CD) was studied using computational approaches. From molecular dynamics simulations, two possible inclusion complexes formed by the chromone ring (C-ring, Form I) and the phenyl ring (P-ring, Form II) of 3HF insertion to γ-CD were observed. Form II is likely more stable because of lower fluctuation of 3HF inside the hydrophobic cavity and lower water accessibility to the encapsulated 3HF. Next, the conformation analysis of these models in the ground (S0) and the first excited (S1) states was carried out by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations, respectively, to reveal the photophysical properties of 3HF influenced by the γ-CD. The results show that the intermolecular hydrogen bonding (interHB) between 3HF and γ-CD, and intramolecular hydrogen bonding (intraHB) within 3HF are strengthened in the S1 state confirmed by the shorter interHB and intraHB distances and the red-shift of O–H vibrational modes involving in the ESPT process. The simulated absorption and emission spectra are in good agreement with the experimental data. Significantly, in the S1 state, the keto form of 3HF is stabilized by γ-CD, explaining the increased quantum yield of keto emission of 3HF when complexing with γ-CD in the experiment. In the other word, ESPT of 3HF is more favorable in the γ-CD hydrophobic cavity than in aqueous solution.

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“…This intramolecular hydrogen bond is more susceptible to interference by fluoride ions, resulting in deprotonation of the -OH group of the probe. 46 Delightfully, the emitter TPA-SYQ exhibited evident and unique discolor observed with the naked eye and green fluorescence change responses to the F À ion competing among the various anions including F À , Cl À , Br À , I À , BF 4 À , PF 6 À , ClO 4 À , H 2 PO 4 À , HSO 4 À , HCO 3 À A C O À , and NO 3 À . Consequently, UV-Vis absorption experiments were initially investigated in MeCN solution for the anion sensing properties.…”

Section: Anion Sensingmentioning

confidence: 98%

Detection of volatile organic compounds, water in organic solvents, and anions using all-in-one type fluorescent emitters, and their data protection applications

Chen

et al. 2022

J. Mater. Chem. C

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Tunable excited-state intramolecular proton transfer reactions with N H or O H as a proton donor: A theoretical investigation

Cited by 36 publications

References 47 publications

Theoretical insights into excited‐state process for the novel 2,3‐bis[(4‐diethylamino‐2‐hydroxybenzylidene)amino]but‐2‐enedinitrile system

Theoretical insights into excited‐state process for the novel 2,3‐bis[(4‐diethylamino‐2‐hydroxybenzylidene)amino]but‐2‐enedinitrile system

Effect of Water Microsolvation on the Excited-State Proton Transfer of 3-Hydroxyflavone Enclosed in γ-Cyclodextrin

Detection of volatile organic compounds, water in organic solvents, and anions using all-in-one type fluorescent emitters, and their data protection applications

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