Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxyacetophenone, salicylamide, and related molecules

Nishiya, T.; Yamauchi, Seigo; Hirota, Noboru; Baba, Masaaki; Hanazaki, Ichiro

doi:10.1021/j100280a053

Cited by 170 publications

(114 citation statements)

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“…The long-wavelength peak of this structure in the excitation spectrum is at about 359 nm (at room temperature at about 366 nm), and we think that this value corresponds to the 0-0 transition in excitation (absorption). It is in full agreement with the value of 358.7 nm, previously found for SAM as guest molecule in durene mixed crystal [9]. The Stokes shift of SAM fluorescence in polycrystal, which amounts to about 6500 cm -1 and is weakly temperature dependent, is considerably reduced compared to the one in solutions, which is about 10000 cm -1 in hydrocarbon and some aqueous liquid solutions, and about 8000 cm -1 in ethanolic glass solution at 77 K. Also, there is a substantial expansion of the range of the absorption, and especially of the excitation spectrum, on the longwave side towards the region of 340-370 nm.…”

Section: Resultssupporting

confidence: 92%

“…An ab initio calculation, performed later [7], showed that the most stable conformer is the cis-form (a) and less stable (by 18.60 kJ/mol) is the trans-form (c). Examination of SAM by two-step laser excitation [8] and high-resolution fluorescence spectroscopy in mixed durene crystal [9], as well as recent theoretical consideration [10], indicate that the zwitterionic form has no counterpart in the ground state. This fact makes possible to use SAM as an active medium in proton-transfer laser [11].…”

Section: Introductionmentioning

confidence: 95%

“…An exception is the study in durene mixed crystal at 4.2 K [9]. In this work, the luminescence and excitation spectra of SAM, recorded for different solid solutions and polycrystalline form at both room temperature and 77 K, were examined.…”

Section: Introductionmentioning

confidence: 99%

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Electronic Spectra of Salicylamide in Polycrystalline Form and Solid Environment

1999

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The fluorescence emission of crystalline salicylamide (λ max = 426 nm, Stokes shift 6500 cm -1 ) is attributed to the proton-transferred species. We suppose that the peak at 359 nm in the substructure of fluorescence excitation spectrum at 77 K is in fact the position of the 0-0 transition. The luminescence and excitation spectra of protolytic forms (anion, neutral molecule and cation) of salicylamide in solid solutions were also examined, as well as the equilibria and photoprocesses in the excited state.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 95%

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Electronic Spectra of Salicylamide in Polycrystalline Form and Solid Environment

1999

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“…13,[32][33][34][35][36][37][38][39] This process is enabled by the nitro groups of EB that are good hydrogen-bond acceptors. [24][25][26]40,41 In order to further confirm this hypothesis, TA measurements were carried out in perdeuterated water.…”

Section: Articlementioning

confidence: 99%

Ultrafast Excited-State Dynamics of Eosin B: A Potential Probe of the Hydrogen-Bonding Properties of the Environment

2011

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The photophysics of two dyes from the xanthene family, eosin B (EB), and eosin Y (EY) has been investigated in various solvents by femtosecond transient absorption spectroscopy, first, to clarify the huge disparity of the EB fluorescence lifetimes reported in literature, and, second, to understand the mechanism responsible for the ultrafast excited-state deactivation of EB in water. The excited-state lifetime of EB was found to be much shorter in water and in other protic solvents, due to the occurrence of hydrogen-bond assisted nonradiative deactivation. This mechanism is associated with the hydrogen bonds between the solvent molecules and the nitro groups of EB, which become stronger upon optical excitation due to the charge-transfer character of the excited-state. This process is not operative with EY, where the nitro groups are replaced by bromine atoms. Therefore, the excited-state lifetime of EB in solution is directly related to the strength of the solvent as a hydrogen-bond donor, offering the possibility to build a corresponding scale based on the fluorescence quantum yield or lifetime of EB. This scale of hydrogen-bonding strength could be especially useful for studies of liquid interfaces by time-resolved surface second harmonic generation

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“…[17][18][19][20][21] The deactivation via hydrogen-bond-assisted proton transfer has been reported for methyl salicylate, 22 anthraquinones, 23,24 and some other aromatic molecules. [25][26][27][28][29][30] A fast deactivation of the photoexcited state was also found with o-aminoacetophenone (AAP) and its derivatives, whose chemical structures are similar to that of KN. 31,32 It has been shown that internal conversion (IC) is the main decay channel of the S 1 state, and that its rate constant is highly sensitive to the solvent: in polar aprotic solvents, the fluorescence lifetime of AAP exceeds 1 ns, while in polar protic and nonpolar solvents it decreases by one and two orders of magnitude.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Excited-State Dynamics of Kynurenine, a UV Filter of the Human Eye

et al. 2009

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The excited-state dynamics of kynurenine (KN) has been examined in various solvents by femtosecondresolved optical spectroscopy. The lifetime of the S 1 state of KN amounts to 30 ps in aqueous solutions, increases by more than 1 order of magnitude in alcohols, and exceeds 1 ns in aprotic solvents such as DMSO and DMF, internal conversion (IC) being shown to be the main deactivation channel. The IC rate constant is pH independent but increases with temperature with an activation energy of about 7 kJ/mol in all solvents studied. The dependence on the solvent proticity together with the observation of a substantial isotope effect indicates that hydrogen bonds are involved in the rapid nonradiative deactivation of KN in water. These results give new insight into the efficiency of KN as a UV filter and its role in cataractogenesis.

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Fluorescence studies of intramolecularly hydrogen-bonded o-hydroxyacetophenone, salicylamide, and related molecules

Cited by 170 publications

References 0 publications

Electronic Spectra of Salicylamide in Polycrystalline Form and Solid Environment

Electronic Spectra of Salicylamide in Polycrystalline Form and Solid Environment

Ultrafast Excited-State Dynamics of Eosin B: A Potential Probe of the Hydrogen-Bonding Properties of the Environment

Ultrafast Excited-State Dynamics of Kynurenine, a UV Filter of the Human Eye

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