The photodynamics of 2-(2′-hydroxy-5′-methylphenyl)-benzotriazole in low-temperature organic glasses

Flom, Steven R.; Barbara, P. F.

doi:10.1016/0009-2614(83)85038-6

Cited by 79 publications

(47 citation statements)

References 20 publications

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“…The l max value found in 400 mM PVP-water mixture indicates that the dielectric constant of the microenvironment of 3HNA is about 21. It is reported that in many organic assemblies, the dielectric constant of confined water is close to that of alcohol (e¼30) [42][43][44]. Thus our results of the micro-polarity of the probe (e ¼21) indicates that water structure where 3HNA gets absorbed is different from that of bulk water and could be speculated as either type I or type II or both types of water as reported by Xu et al [10].…”

Section: Viscosity and Polarity Of The Microenvironment Around The Flsupporting

confidence: 71%

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Pal

Maity

Samanta

et al. 2010

Journal of Luminescence

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Section: Viscosity and Polarity Of The Microenvironment Around The Flsupporting

confidence: 71%

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Pal

Maity

Samanta

et al. 2010

Journal of Luminescence

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“…So, they have generated a considerable amount of interest. [1][2][3][4][5] Excited state proton transfer ͑ESPT͒ in hydrogen-bonded systems such as benzimidazoles, in particular, has attracted a lot of attention. 6,7 The ESPT of the cationic form of 2-͑2Ј-pyridyl͒benzimidazole ͑2PBI͒ is manifested in a distinct dual emission in its aqueous solutions in the pH range of 3.5-0.5 ͑Scheme 1͒.…”

Section: Introductionmentioning

confidence: 99%

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Burai

Mukherjee²,

Lahiri³

et al. 2009

The Journal of Chemical Physics

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2-͑2Ј-pyridyl͒benzimidazole ͑2PBI͒ undergoes excited state proton transfer ͑ESPT͒ in acidic solutions, leading to a tautomer emission at 460 nm. This photoprocess has been studied using ultrafast fluorescence spectroscopic techniques in acidic neat aqueous solutions, in viscous mixtures of glycerol with water, as well as in sucrose solutions. The tautomer is found to be stabilized in the more viscous medium, leading to a greater relative quantum yield as well as lifetime. The long rise time in tautomer emission is not affected by viscosity though. Rather, it appears to have the same value as the long component of the decay of the cationic excited state ͑C ‫ء‬ ͒. In addition to the subnanosecond lifetime reported earlier, C ‫ء‬ is found to exhibit a decay time of 2 ps. This is assigned to its protonation to form the nonfluorescent dication in its excited state ͑D ‫ء‬ ͒ considering the ground and excited state pK a values reported earlier. An additional rising component of 100 ps is observed in the region of C ‫ء‬ emission. This is likely to arise from a structural change or charge redistribution in C ‫ء‬ immediately after its creation and before the phototautomerization.

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“…The huge potential in the ESIPT process has provoked massive interest among the photophysicists and photochemists. Studies range from the choice of a variety of homo-and heterocyclic aromatic molecular systems to a wide variety of pure and mixed homogeneous and microheterogeneous solvents [1][2][3][4][5][6][7][8][9][10][11]. This phenomenon has widespread implications in photostabilizers [12], laser dyes [13] and also in the biological fields [14].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

Purkayastha

Chattopadhyay

2003

IJMS

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Two series of compounds, one comprising of 2-(2′-hydroxyphenyl)benzoxazole (HBO), 2-(2′-hydroxyphenyl)benzimidazole (HBI), 2-(2′-hydroxyphenyl)benzothiazole (HBT), and the other of 2-(2′-hydroxyphenyl)oxazole (HPO), 2-(2′-hydroxyphenyl)imidazole (HPI) and 2-(2′-hydroxyphenyl)thiazole (HPT) are susceptible to ground state rotamerization as well as excited state intramolecular proton transfer (ESIPT) reactions. Some of these compounds show experimental evidence of the existence of two ground state conformers. Out of these two one undergoes ESIPT reaction leading to the formation of the tautomer. The two photophysical processes, in combination, result in the production of a number of fluorescence bands each one of which corresponding to a particular species. Semiempirical AM1-SCI calculations have been performed to rationalize the photophysical behaviour of the compounds. The calculations suggest that for the first series of compounds, two rotational isomers are present in the ground state of HBO and HBI while HBT has a single conformer under similar circumstances. For the molecules of the other series existence of rotamers depends very much on the polarity of the environment. The potential energy curves (PEC) for the ESIPT process in different electronic states of the molecules have been generated theoretically. The simulated PECs reveal that for all these systems the IPT reaction is unfavourable in the ground state but feasible, both kinetically and thermodynamically, in the S 1 as well as T 1 states.

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The photodynamics of 2-(2′-hydroxy-5′-methylphenyl)-benzotriazole in low-temperature organic glasses

Cited by 79 publications

References 20 publications

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Interaction of the excited state intramolecular proton transfer probe 3-hydroxy-2-naphthoic acid with poly N-vinyl-2-pyrrolidone polymer in water: An insight into the water structure in the binding region

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Theoretical Modelling for the Ground State Rotamerisation and Excited State Intramolecular Proton Transfer of 2-(2’-hydroxyphenyl)oxazole, 2-(2’-hydroxyphenyl)imidazole, 2-(2’-hydroxyphenyl)thiazole and Their Benzo Analogues

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