Photophysical Properties of an Azine-Linked Pyrene–Cinnamaldehyde Hybrid: Evidence of Solvent-Dependent Charge-Transfer-Coupled Excimer Emission

Bhattacharyya, Arghyadeep; Makhal, Subhash Chandra; Guchhait, Nikhil

doi:10.1021/acsomega.8b02717

Cited by 13 publications

(2 citation statements)

References 50 publications

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“…This indicates that the protonated species acquired more stability by charge transfer from the hydroxyl group. 46 After the base was added, the band at 358 nm shrank and a new red shifted band of the anionic species appears at 440 nm (Fig. 9B).…”

Section: Resultsmentioning

confidence: 96%

Switching of photoinduced proton transfer from one six-membered hydrogen-bonded ring to other: a molecule of hydrazine and pH sensor

Bhakta,

Guchhait

2024

Phys. Chem. Chem. Phys.

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Section: Resultsmentioning

confidence: 96%

Switching of photoinduced proton transfer from one six-membered hydrogen-bonded ring to other: a molecule of hydrazine and pH sensor

Bhakta,

Guchhait

2024

Phys. Chem. Chem. Phys.

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“…As is known to all, the photo-induced proton transfer (i.e., excited-state intramolecular or intermolecular proton transfer [ESIPT]), photo-induced charge transfer (CT), and photo-induced energy transfer are deemed to become the most elementary and vital excited state dynamical reactions in a variety of chemical processes and biological fields. [1][2][3][4][5][6][7][8] Particularly, since the ESIPT reaction was reported for the first time about half a century ago, [9] ESIPT reaction has received wide attention due to its potential applications. [9][10][11][12][13][14][15][16] In fact, ESIPT reaction occurs along with hydrogen bond, which belongs to a kind of acid-base neutralization process.…”

Section: Introductionmentioning

confidence: 99%

Revelation of ESIPT mechanism for the novel fluorescent system HNIBT in toluene and methanol solvents: A TDDFT study

Feng

et al. 2020

J Chinese Chemical Soc

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In this work, we devote to explore excited‐state intramolecular proton transfer (ESIPT) behavior for a novel fluorescent molecule naphthalimide‐based 2‐(2‐hydroxyphenyl)‐benzothiazole (HNIBT) [New J. Chem. 2019, 43, 9152.] in toluene and methanol (MeOH) solvents. Exploring weak interactions, stable HNIBT‐enol, and HNIBT‐MeOH‐enol complex can be found in S0 state via TDDFT/B3LYP/6‐311+G(d,p) level. Given photoexcitation, intramolecular hydrogen bond O1H2···N3 of HNIBT‐enol and HNIBT‐MeOH‐enol is dramatically enhanced, which offers impetus for facilitates ESIPT reaction. After repeated comparisons, we verify the unavailability of intermolecular hydrogen bonding effects between HNIBT‐enol and MeOH molecules. In view of excitation, HOMO (π) → LUMO (π*) transition and the changes of electronical densities indeed impulse ESIPT tendency. Via constructing potential energy curves (PECs), for both HNIBT‐enol and HNIBT‐MeOH‐enol complex, the ESIPT could only occur along with intramolecular hydrogen bond O1H2···N3. Through comparison, the potential barrier falls from 4.124 kcal/mol (HNIBT‐enol) to 2.132 kcal/mol (HNIBT‐MeOH‐enol). Therefore, we confirm that the ESIPT of the HNIBT system happens more easily in the MeOH solvent compared with the toluene solvent.

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Theoretical investigation of excited state charge and proton transfer mechanism for the novel 10‐methyl‐indolo[2,3‐a]‐indolo[2,3‐a′]acridone molecule

Yang

Chen

Jin

et al. 2020

J of Physical Organic Chem

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A novel acridone derivative, 10‐methyl‐indolo[2,3‐a]‐indolo[2,3‐a′]acridone (13), was reported by Fang and coworkers [J. Org. Chem. 2019, 84, 3832] in a previous paper. Spectroscopic studies on excited‐state intramolecular proton transfer (ESIPT) of 13 were mentioned, while the mechanism of ESIPT for 13 is deficiency. In this present work, based on the time dependent density functional theory (TDDFT), we investigated the ESIPT mechanism of 13 theoretically. The primary bond lengths, bond angles and the infrared (IR) vibrational spectra involved in the formation of hydrogen bonds verified that the intramolecular hydrogen bond should be strengthened, which manifests the tendency of excited state proton transfer. The redistribution of charge resulting from photoexcitation process reveals the driving force for ESIPT process. According to the results of theoretical potential energy curves along N‐H coordinate, an about 14.825 kcal/mol barrier has been found in the S0 state. However, a low barrier of 6.708 kcal/mol was calculated in the S1 state, which demonstrates that the proton transfer process is more likely to occur in the excited state. In other words, the proton transfer was facilitated by photoexcitation. Particularly, the study about ESIPT mechanism of 13 should be helpful for further understanding property of acridone derivatives.

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Photophysical Properties of an Azine-Linked Pyrene–Cinnamaldehyde Hybrid: Evidence of Solvent-Dependent Charge-Transfer-Coupled Excimer Emission

Cited by 13 publications

References 50 publications

Switching of photoinduced proton transfer from one six-membered hydrogen-bonded ring to other: a molecule of hydrazine and pH sensor

Switching of photoinduced proton transfer from one six-membered hydrogen-bonded ring to other: a molecule of hydrazine and pH sensor

Revelation of ESIPT mechanism for the novel fluorescent system HNIBT in toluene and methanol solvents: A TDDFT study

Theoretical investigation of excited state charge and proton transfer mechanism for the novel 10‐methyl‐indolo[2,3‐a]‐indolo[2,3‐a′]acridone molecule

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