Theoretical insights into the ultrafast excited-state intramolecular proton transfer (ESIPT) mechanism in a series of amide-based N H⋯N hydrogen-bonding compounds

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

doi:10.1016/j.orgel.2017.02.034

Cited by 42 publications

(15 citation statements)

References 46 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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“…The premier ESIPT species was first reported by Weller et al [15]. Since then, ESIPT has shown a variety of potential applications in many biological, chemical, physical and other fields, such as laser dyes [16], white light emitting materials [17], molecular switches [18,19], fluorescence sensors [20][21][22][23][24][25] and so on [26,27]. Moreover, the ESIPT fluorophore is characterized by its ultra-fast time scale [28,29] and large Stokes displacement [30].…”

Section: Introductionmentioning

confidence: 99%

Solvent effect on the excited-state intramolecular double proton transfer of 1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole

Liu

Wang

et al. 2021

Photochem Photobiol Sci

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Density functional theory (DFT) and time-dependent density functional theory (TDDFT) are used to study the solvatochromic effect and the excited-state intramolecular double proton transfer (ESIDPT) of 1,3-Bis(2-pyridylimino)-4,7-dihydroxyisoindole (BPI-OH) in different kinds of solvents. The hydrogen bonding parameters and IR spectra reveal that in the excited state, the strength of excited hydrogen bond increase with the decrease of solvent polarity. Furthermore, the reduction density gradient (RDG) analysis confirms the corresponding conclusion. Frontier molecular orbitals (FMOs) are analyzed, illuminating that the smaller the polarity of solvent, the smaller the energy gap between the HOMO and LUMO. The structures of BPI-OH (N) (normal), BPI-OH (T 1 ) (single), and BPI-OH (T 2 ) (double) were optimized. Previous reports found the double protons in BPI-OH molecule are transferred step-by-step process BPI-OH(N)→BPI-OH(T 1 )→BPI-OH(T 2 ) in the ground state (S 0 ) and the first excited singlet state (S 1 ). Here, the potential energy curves of O 1 -H 2 and O 4 -H 5 in the S 0 and S 1 states were scanned in four kinds of solvents, respectively. It was found that in S 1 state, BPI-OH(N)→BPI-OH(T 1 ) was more prone to proton transfer than BPI-OH(T 1 )→BPI-OH(T 2 ). In addition, by comparing the reaction energy barriers of the four kinds of solvents, it can be found that ESIPT is difficult to occur with the increase of solvent polarity. Meanwhile, it was also studied that MeOH as an explicit solvent was more likely to promote the ESIPT process than other implicit solvents.

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“…Hydrogen bond (HB) observed in DNA, water, proteins, and other materials (Zhao and Han, 2011;Tanioku et al, 2013;Gole et al, 2014;Ling and Gutowski, 2016;Huang et al, 2018) formed between a hydrogen (H) atom of one molecular fragment D-H and another atom A (i.e., D-H ... A) (Li et al, 2011;Wilcken et al, 2013;An et al, 2016An et al, , 2017Ma et al, 2018;Zhao et al, 2019). Where D atom is connected to H atom by a covalent bond (or ionic bond), the A atom has a high electron density and is easy to attract hydrogen proton.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Sensing Mechanism of Novel Hydrazine Sensor TAPHP and Its ESIPT and ICT Processes

Liu

et al. 2020

Front. Chem.

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The photophysical and photochemical properties of the novel hydrazine sensor TAPHP and the TAPDP generated by the cyclization reaction of TAPHP with hydrazine are investigated using the density functional theory and time-dependent density functional theory. The results show that both the excited-state intramolecular proton transfer and intramolecular charge transfer can occur for TAPHP and TAPDP. Analysis of bond parameters and infrared vibrational spectra indicate that hydrogen bonds are enhanced in the first excited state, which is beneficial to excited-state intramolecular proton transfer. The strength of hydrogen bonds is also visualized by using the independent gradient model and topological analysis. The core-valence bifurcation index and bond critical point parameters are further employed to measure hydrogen bonds. The reaction path of proton transfer is obtained through the potential energy curves. The excitation of TAPHP and TAPDP is attributed to the charge transfer excitation, which is determined by the characteristics of the hole-electron distribution. The reaction site and product configuration are verified by atomic charge and 1 H-NMR spectra. The negative free energy difference indicates that the reaction between TAPHP and hydrazine can proceed spontaneously. In addition, the absorption and fluorescence spectra agree well with the experimental results, confirming that TAPHP is an excellent sensor of hydrazine.

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Theoretical insights into the ultrafast excited-state intramolecular proton transfer (ESIPT) mechanism in a series of amide-based N H⋯N hydrogen-bonding compounds

Cited by 42 publications

References 46 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

Solvent effect on the excited-state intramolecular double proton transfer of 1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole

Theoretical Study on the Sensing Mechanism of Novel Hydrazine Sensor TAPHP and Its ESIPT and ICT Processes

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