Solvation effect on the ESIPT mechanism of 2-(4′-amino-2′-hydroxyphenyl)-1H-imidazo-[4,5-c]pyridine

Tang, Zhe; Lu, Ming; Liu, Kangjing; Zhao, Yanliang; Qi, Yutai; Wang, Yi; Zhang, Peng; Zhou, Panwang

doi:10.1016/j.jphotochem.2018.08.028

Cited by 39 publications

(7 citation statements)

References 60 publications

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“…Controlling the various factors of ESIPT molecules would contribute to develop new multiemissive materials. ESIPT dynamics have been deeply investigated theoretically and experimentally [31][32][33][34][35][36][37][38][39][40][41][42]. Takagi et al [37] studied the ESIPT fluorescence properties of methoxy-substituted 2-hydroxyphenylbenzimidazole.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigations on forward–backward ESIPT processes of three fluorophores deriving from 2-(2′-hydroxyphenyl)thiazole

Liang

Fang

2021

Photochem Photobiol Sci

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The photophysical properties and excited-state intramolecular proton transfer (ESIPT) processes for 2-(2′-hydroxyphenyl)-4-chloromethylthiazole (1), 2-(2′-hydroxyphenyl)-4-phenylthiazole (2), 2-(2′-hydroxyphenyl)-4-hydroxymethyl-thiazole (3) were studied at the TD-B3PW91/6-31 + G(d, p)/IEFPCM level. The structures of 1-3 were fully optimized and the corresponding structural parameters, infrared spectra and electron densities in the ground (S 0 ) and the first excited (S 1 ) states were analyzed. The calculated absorption and fluorescence wavelengths of 1-3 reproduced the experimental data. The potential energy curves of the S 0 and S 1 states were built and the ESIPT processes were clarified. Our results showed that the intramolecular H-bonds of 3 and 2 in the S 1 state were the strongest and the weakest, respectively, and then the ESIPT potential barriers of 3 and 2 were the lowest and highest, respectively. Among the three phenol-thiazole type probes, the compound 2 with phenyl ring group at the 4 position of the thiazole ring had the larger π-conjugation, and had the higher ESIPT potential barrier at the same time. The corresponding compound 1 and 3 with CH 2 Cl and CH 2 OH had the lower ESIPT barrier.

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Section: Introductionmentioning

confidence: 99%

Theoretical investigations on forward–backward ESIPT processes of three fluorophores deriving from 2-(2′-hydroxyphenyl)thiazole

Liang

Fang

2021

Photochem Photobiol Sci

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“…Therefore, the solvent polarity modulation of fluorescence was quite interesting. It was well studied that amide tautomer of pyrazolopyridopyridazine dione 6a was efficiently produced in toluene, THF, EA, and CH 2 Cl 2 solvents [39][40][41][42][43][44]. In alcoholic (protic) and DMSO solvent, there exists competition between intermolecular bonding of the nearest hydrogen with the hydroxyimine tautomer of 6-hydroxypyrazolopyridopyridazin-9-one 6a.…”

Section: Resultsmentioning

confidence: 99%

Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

et al. 2020

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The newly designed luminol structures of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were synthesized from versatile 1,3-diaryfuropyrazolopyridine-6,8-diones, 1,3-diarylpyrazolopyrrolopyridine-6,8-diones, or 1,3-diaryl-7-methylpyrazolopyrrolopyridine-6,8-diones with hydrazine monohydrate. Photoluminescent and solvatofluorism properties containing UV–Vis absorption, emission spectra, and quantum yield (Φf) study of pyrazolopyridopyridazine diones and N-aminopyrazolopyrrolopyridine diones were also studied. Generally, most of pyrazolopyrrolopyridine-6,8-diones 6 exhibited the significant fluorescence intensity and the substituent effect when compared with N-aminopyrazolopyrrolopyridine diones, particularly for 6c and 6j with a m-chloro group. Additionally, the fluorescence intensity of 6j was significantly promoted due to the suitable conjugation conformation. Based on the quantum yield (Φf) study, the value of compound 6j (0.140) with planar structural skeletal was similar to that of standard luminol (1, 0.175).

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“…In addition, ESIPT is sensitive to the polarity of solvent and types of solvent [31]. According to this conclusion, the ESIPT and fluorescent mechanisms have been studied by many groups [11,32,33].…”

Section: Introductionmentioning

confidence: 94%

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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Solvation effect on the ESIPT mechanism of 2-(4′-amino-2′-hydroxyphenyl)-1H-imidazo-[4,5-c]pyridine

Cited by 39 publications

References 60 publications

Theoretical investigations on forward–backward ESIPT processes of three fluorophores deriving from 2-(2′-hydroxyphenyl)thiazole

Theoretical investigations on forward–backward ESIPT processes of three fluorophores deriving from 2-(2′-hydroxyphenyl)thiazole

Selective Synthesis and Photoluminescence Study of Pyrazolopyridopyridazine Diones and N-Aminopyrazolopyrrolopyridine Diones

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

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