Modulating the ESIPT dynamics of 3HF derivatives via substitution and solvent effect: A theoretical study

Lin, Man-yu; Li, Yanchun; Fu, Cheng-bin; Yu, Xing

doi:10.1016/j.molliq.2022.120295

Cited by 8 publications

(4 citation statements)

References 34 publications

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“…Electronic properties of ESIPT-capable molecules and therefore the ESIPT and GSIPT abilities of such molecules can be tuned through introducing various substituents or heteroatoms, 16–36 expanding the π-system, 37–40 binding metal ions, 41–54 protonation/deprotonation, 55–64 solvent effects, 65–69 etc. The synthetic flexibility of such molecules is based on established synthetic methods of organic chemistry and provides researchers with almost unlimited options for the rational design and modification of various ESIPT-capable scaffolds.…”

Section: Introductionmentioning

confidence: 99%

Dual emission of ESIPT-capable 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of fluorescence and phosphorescence

et al. 2023

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ESIPT-capable pyrimidine-based compounds featuring short O–H···N intramolecular hydrogen bonds, 2-(2-hydroxyphenyl)-4-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidine (HL1) and 2-(2-hydroxyphenyl)-4-(3,5-diphenyl-1H-pyrazol-1-yl)-6-methylpyrimidine (HL2), were synthesized by the condensation of 4-hydrazinyl-2-(2-hydroxyphenyl)-6-methylpyrimidine with acetylacetone and dibenzoylmethane. In solution, HL1 and HL2...

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Section: Introductionmentioning

confidence: 99%

Dual emission of ESIPT-capable 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of fluorescence and phosphorescence

et al. 2023

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“…S10 (ESI †). Due to the existence of a small energy barrier, the ultrafast ESIPT reaction occurs easily, [45][46][47][48][49] which is what have observed experimentally with about 1 ps (Fig. 5).…”

Section: Resultsmentioning

confidence: 78%

Excited-state dynamics of 4-hydroxyisoindoline-1,3-dione and its derivative as fluorescent probes

Zhao,

Jiang,

et al. 2024

Phys. Chem. Chem. Phys.

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“…The ESIPT photoreaction ( Scheme 1 ) is highly sensitive to substituents [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] and coordinated metal ions [ 28 , 29 , 30 , 31 , 32 , 33 ], protonation/deprotonation [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ], the state of aggregation [ 42 , 43 ], the polarity of solvent [ 44 , 45 , 46 , 47 , 48 ] and the presence of various analytes [ 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. If the excited state tautomerization (normal-to-tautomeric) is barrierless, the only form to emit is the tautomeric one, which typically luminesces with rather large Stokes shift [ 57 , 58 ].…”

Section: Introductionmentioning

confidence: 99%

ESIPT-Capable 4-(2-Hydroxyphenyl)-2-(Pyridin-2-yl)-1H-Imidazoles with Single and Double Proton Transfer: Synthesis, Selective Reduction of the Imidazolic OH Group and Luminescence

et al. 2023

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1H-Imidazole derivatives establish one of the iconic classes of ESIPT-capable compounds (ESIPT = excited state intramolecular proton transfer). This work presents the synthesis of 1-hydroxy-4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (LOH,OH) as the first example of ESIPT-capable imidazole derivatives wherein the imidazole moiety simultaneously acts as a proton acceptor and a proton donor. The reaction of LOH,OH with chloroacetone leads to the selective reduction of the imidazolic OH group (whereas the phenolic OH group remains unaffected) and to the isolation of 4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (LH,OH), a monohydroxy congener of LOH,OH. Both LOH,OH and LH,OH demonstrate luminescence in the solid state. The number of OH···N proton transfer sites in these compounds (one for LH,OH and two for LOH,OH) strongly affects the luminescence mechanism and color of the emission: LH,OH emits in the light green region, whereas LOH,OH luminesces in the orange region. According to joint experimental and theoretical studies, the main emission pathway of both compounds is associated with T1 → S0 phosphorescence and not related to ESIPT. At the same time, LOH,OH also exhibits S1 → S0 fluorescence associated with ESIPT with one proton transferred from the hydroxyimidazole moiety to the pyridine moiety, which is not possible for LH,OH due to the absence of the hydroxy group in the imidazole moiety.

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Modulating the ESIPT dynamics of 3HF derivatives via substitution and solvent effect: A theoretical study

Cited by 8 publications

References 34 publications

Dual emission of ESIPT-capable 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of fluorescence and phosphorescence

Dual emission of ESIPT-capable 2-(2-hydroxyphenyl)-4-(1H-pyrazol-1-yl)pyrimidines: interplay of fluorescence and phosphorescence

Excited-state dynamics of 4-hydroxyisoindoline-1,3-dione and its derivative as fluorescent probes

ESIPT-Capable 4-(2-Hydroxyphenyl)-2-(Pyridin-2-yl)-1H-Imidazoles with Single and Double Proton Transfer: Synthesis, Selective Reduction of the Imidazolic OH Group and Luminescence

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