Investigation of the dynamic processes of the excited states of o-hydroxybenzaldehyde and o-hydroxyacetophenone by emission and picosecond spectroscopy

Nagaoka, Shin‐ichi; Hirota, Noboru; Sumitani, Minoru; Yoshihara, Keitaro

doi:10.1021/ja00351a016

Cited by 145 publications

(95 citation statements)

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“…Molecules giving rise to excited state tautomers by intramolecular proton transfer enjoy applications as laser dyes, in higher energy radiation detectors and molecular memory storage devices, as fluorescent probes and also as polymer protecting agents [6].…”

Section: Introductionmentioning

confidence: 99%

Solid state tautomerism in 2-((phenylimino)methyl)naphthalene-1-ol

Nedeltcheva¹,

Kamounah²,

Mirolo³

et al. 2009

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

Solid state tautomerism in 2-((phenylimino)methyl)naphthalene-1-ol

Nedeltcheva¹,

Kamounah²,

Mirolo³

et al. 2009

Dyes and Pigments

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“…Fluorescence measurements in matrices 20 and in the liquid phase [21][22][23] helped to identify the nature of the excited states undergoing ESIPT. Theoretical studies predicted a small 24 or nonexistent barrier 25,26 for the proton transfer and suggested similar reaction dynamics for many ESIPT systems.…”

mentioning

confidence: 99%

Dynamics of excited-state proton transfer systems via time-resolved photoelectron spectroscopy

Lochbrunner

Schultz

Schmitt

et al. 2001

The Journal of Chemical Physics

155

158

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We investigate the applicability of time-resolved photoelectron spectroscopy to excited state intramolecular proton transfer (ESIPT) and internal conversion dynamics in the model system o-hydroxybenzaldehyde (OHBA) and related compounds. Photoelectron spectra of both the excited state enol and keto tautomers were obtained as a function of pump laser wavelength and pump-probe time delay. The ESIPT was found to occur in less than 50 fs over the whole absorption range of the S1(ππ*) state for both OHBA and its monodeuterated analog, suggestive of a small or nonexistent barrier. The subsequent keto internal conversion rate in OHBA varies from 0.63 to 0.17 ps−1 over the S1(ππ*) absorption band and the OD-deuterated analog shows no significant isotope effect. Based upon ab initio calculations and comparison with the two-ring analog, 1-hydroxy-2-acetonaphthone (HAN), we suggest that the internal conversion dynamics in OHBA is influenced by interactions with a close-lying nπ* state.

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“…The values of rate constants show that proton transfer is relatively faster in CMOH than in MFOH (11). However, the process is relatively slower than that observed in the case of other similar compounds such as methyl salicylate (MS) and orthohydroxybenzaldehyde (OHBA) (8,24,35). Slower decay rates indicate stronger interaction of CMOH with solvents compared to MS and OHBA.…”

Section: Fluorescence Decaymentioning

confidence: 92%

“…Nagaoka et al (8) showed that this conversion is extremely slow in the case of o-hydroxyacetophenone (OHAP) and does not take place at all in the case of o-hydroxypropiophenone (OHPP), but occurs easily in the case of o-hydroxybenzaldehyde (OHBA) (8). The phosphorescence was also not observed in the case of methylsalicylate (MS) (33,38).…”

Section: Emission Spectra At 77 Kmentioning

confidence: 99%

“…Solvent effects on proton transfer to solvent raise interesting problems concerning static and dynamic processes. Several spectroscopic studies have shown that compounds such as o-hydroxybenzaldehyde (OHBA) and methylsalicylate (MS) are hydrogen-bonded to the solvent in proton-accepting solvents (8,9). It has been noted in our earlier study that both the absorption and emission spectra and the decay rate of 4-methyl-2,6-diacetylphenol (MAOH) are considerably different from those of 4-methyl-2,6-diformylphenol (MFOH) despite the similarity in molecular structure (1)(2)(3)7).…”

Section: Introductionmentioning

confidence: 99%

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