TDDFT Assessment of Excited State Intramolecular Proton Transfer in a Panel of Chromophore 2-Hydroxypyrene-1-Carbaldehyde

Shi, Yanrong

doi:10.4208/jams.022016.041016a

Cited by 22 publications

(3 citation statements)

References 40 publications

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“…Moreover, from the ground equilibrium structures, the S 1 state was optimized by analyzing vibrational frequencies with the TDDFT method to ensure the local minima on S 1 PES. Herein, it is worth mentioning that the TDDFT method has become a very useful tool for theoretically investigating hydrogen bonding in the excited states of hydrogen-bond systems, [48][49][50][51][52][53][54][55][56] even though this kind of calculation is very time consuming. The PESs of the S 0 and S 1 states were also carried out for the proton-transfer process in EtOH.…”

Section: Computational Detailsmentioning

confidence: 99%

“…Furthermore, hydrogen bond strengthening or weakening could also be revealed based on monitoring the spectral shifts of vibrational modes involved in the formation of hydrogen bonds. [5][6][7][8][9][48][49][50][51][52][53][54][55][56] The vibrational spectra of the ASI chromophore in the conjunct vibrational regions of the O 1 -H 2 and O 5 -H 6 stretching bands are shown in Fig. 2.…”

Section: Geometric Structuresmentioning

confidence: 99%

“…47 However, spectroscopic techniques such as absorption and emission spectra, time-resolved fluorescence spectroscopy, and so on could only provide some indirect information about photophysical or photochemical properties. [48][49][50][51][52][53][54][55][56] Moreover, the specific excited-state dynamic process of ASI about ESIPT is insufficient. 47 Particularly, because the nodal plane model is not very accurate, we doubt whether there is a synergetic or sequential double-proton transfer process.…”

Section: Introductionmentioning

confidence: 99%

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A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I

et al. 2018

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The excited-state proton transfer (ESPT) dynamical behavior of aloesaponarin I (ASI) was studied using density functional theory (DFT) and time-dependent DFT (TDDFT) methods. Our calculated vertical excitation energies based on TDDFT reproduced the experimental absorption and fluorescence spectra well [Nagaoka et al. J. Phys. Chem. B, 117, 4347 (2013)]. Two intramolecular hydrogen bonds were confirmed to be strengthened in the S1 state, which makes ESPT possible. Herein, the ESPT process is more likely to happen, along with one hydrogen bond (O1–H2⋯O3). Qualitative analyses about charge distribution further demonstrate that the ESPT process could occur because of the intramolecular charge transfer. Our constructed potential energy surfaces of both S0 and S1 states show that a single proton transfer reactive is more reasonable along with the intramolecular hydrogen bond (O1–H2⋯O3) rather than O4–H5⋯O6 in the S1 stated potential energy surface. Then, ASI-SPT* decays to the ground state with a 640 nm fluorescence; subsequently, the ASI-SPT form shows that reverse ground state single-proton transfer back to the ASI structure occurs. Particularly, dependent on relatively accurate potential energy barriers among these excited-state stable structures, we confirmed the excited-state single proton transfer process rather than using the controversial nodal plane model.

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Section: Computational Detailsmentioning

confidence: 99%

Section: Geometric Structuresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I

et al. 2018

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Different ESIPT Mechanisms forAngular‐Shaped Quinacridone in Toluene and Dimethyl Formamide (DMF) Solvents: A Theoretical Study

Yang

Jia

Song

et al. 2018

J Chinese Chemical Soc

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Adopting density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods, we investigat and present two different excited-state intramolecular proton transfer (ESIPT) mechanisms of angular-quinacridone (a-QD) in both toluene and DMF,theoretically. Comparing the primary structural variations of a-QD involved in the intramolecular hydrogen bond, we conclude that N1-H2Á Á ÁO3 should be strengthened in the S 1 state, which may facilitate the ESIPT process. Particularly, in toluene, the S 1 -state-stable a-QD enol* could not be located because of the non-barrier ESIPT process. Concomitantly, infrared vibrational spectral analysis further verified the stability of the hydrogen bond. In addition, the role of charge-transfer interaction has been addressed under the frontier molecular orbitals (MOs), which depicts the nature of the electronic excited state and supports the ESIPT reaction. The potential energy curves according to variational N1-H2 coordinate demonstrates that the proton transfer process should occur spontaneously in toluene; however, in DMF, a low potential energy barrier of 0.493 kcal/mol is needed to complete the ESIPT reaction. Although this barrier of 0.493 kcal/ mol is too low to make an important impact on the ESIPT reaction, just because of the existence of barrier, ESIPT mechanisms in toluene and DMF are different.

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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

Tong

2018

J Chinese Chemical Soc

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TDDFT Assessment of Excited State Intramolecular Proton Transfer in a Panel of Chromophore 2-Hydroxypyrene-1-Carbaldehyde

Cited by 22 publications

References 40 publications

A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I

A theoretical investigation on excited-state single or double proton transfer process for aloesaponarin I

Different ESIPT Mechanisms forAngular‐Shaped Quinacridone in Toluene and Dimethyl Formamide (DMF) Solvents: A Theoretical Study

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

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