Temperature Effect on Dual Fluorescence of 2‑(2′-Hydroxyphenyl)benzimidazole and Its Nitrogen Substituted Analogues

The effects of temperature on the dual fluorescence of 2-(2′-hydroxyphenyl)benzimidazole (HPBI) and its nitrogen substituted analogues, viz., 2-(2′-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine (HPIP-b) and 2-(2′-hydroxyphenyl)-1H-imidazo[4,5-c]pyridine (HPIP-c), were investigated in solvents of differen...

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Veröffentlicht in:The journal of physical chemistry. B 2013-11, Vol.117 (45), p.14079-14088
Hauptverfasser: Chipem, Francis A. S, Krishnamoorthy, Govindarajan
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container_end_page 14088
container_issue 45
container_start_page 14079
container_title The journal of physical chemistry. B
container_volume 117
creator Chipem, Francis A. S
Krishnamoorthy, Govindarajan
description The effects of temperature on the dual fluorescence of 2-(2′-hydroxyphenyl)benzimidazole (HPBI) and its nitrogen substituted analogues, viz., 2-(2′-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine (HPIP-b) and 2-(2′-hydroxyphenyl)-1H-imidazo[4,5-c]pyridine (HPIP-c), were investigated in solvents of different polarity and hydrogen bonding capability. Absorption, steady-state, and time-resolved emission spectroscopic techniques were employed for the experimental study. Density functional theoretical calculations were performed to find the relative population of the conformers. The calculations predict that, with increase in temperature, the population of trans-enol increases, while that of cis-enol decreases. At all temperatures, the population ratio of cis-enol to trans-enol increases in the order HPIP-c < HPIP-b < HPBI. Except for HPBI in methanol and ethylene glycol, the fluorescence of both emissions decreases with an increase in temperature and is more pronounced in the tautomer band than in the normal band. The data are analyzed using the Arrhenius and van’t Hoff equations. The change in the fluorescence with temperature is governed by (i) the change in the relative population of conformers and (ii) the increase in non-radiative decay from the excited states. The increase in non-radiative decay from the normal emission competes with the increase in the relative population of trans-enol with a rise in temperature.
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S ; Krishnamoorthy, Govindarajan</creator><creatorcontrib>Chipem, Francis A. S ; Krishnamoorthy, Govindarajan</creatorcontrib><description>The effects of temperature on the dual fluorescence of 2-(2′-hydroxyphenyl)benzimidazole (HPBI) and its nitrogen substituted analogues, viz., 2-(2′-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine (HPIP-b) and 2-(2′-hydroxyphenyl)-1H-imidazo[4,5-c]pyridine (HPIP-c), were investigated in solvents of different polarity and hydrogen bonding capability. Absorption, steady-state, and time-resolved emission spectroscopic techniques were employed for the experimental study. Density functional theoretical calculations were performed to find the relative population of the conformers. The calculations predict that, with increase in temperature, the population of trans-enol increases, while that of cis-enol decreases. At all temperatures, the population ratio of cis-enol to trans-enol increases in the order HPIP-c &lt; HPIP-b &lt; HPBI. Except for HPBI in methanol and ethylene glycol, the fluorescence of both emissions decreases with an increase in temperature and is more pronounced in the tautomer band than in the normal band. The data are analyzed using the Arrhenius and van’t Hoff equations. The change in the fluorescence with temperature is governed by (i) the change in the relative population of conformers and (ii) the increase in non-radiative decay from the excited states. 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S</creatorcontrib><creatorcontrib>Krishnamoorthy, Govindarajan</creatorcontrib><title>Temperature Effect on Dual Fluorescence of 2‑(2′-Hydroxyphenyl)benzimidazole and Its Nitrogen Substituted Analogues</title><title>The journal of physical chemistry. B</title><addtitle>J. Phys. Chem. B</addtitle><description>The effects of temperature on the dual fluorescence of 2-(2′-hydroxyphenyl)benzimidazole (HPBI) and its nitrogen substituted analogues, viz., 2-(2′-hydroxyphenyl)-3H-imidazo[4,5-b]pyridine (HPIP-b) and 2-(2′-hydroxyphenyl)-1H-imidazo[4,5-c]pyridine (HPIP-c), were investigated in solvents of different polarity and hydrogen bonding capability. Absorption, steady-state, and time-resolved emission spectroscopic techniques were employed for the experimental study. Density functional theoretical calculations were performed to find the relative population of the conformers. The calculations predict that, with increase in temperature, the population of trans-enol increases, while that of cis-enol decreases. At all temperatures, the population ratio of cis-enol to trans-enol increases in the order HPIP-c &lt; HPIP-b &lt; HPBI. Except for HPBI in methanol and ethylene glycol, the fluorescence of both emissions decreases with an increase in temperature and is more pronounced in the tautomer band than in the normal band. The data are analyzed using the Arrhenius and van’t Hoff equations. The change in the fluorescence with temperature is governed by (i) the change in the relative population of conformers and (ii) the increase in non-radiative decay from the excited states. 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Absorption, steady-state, and time-resolved emission spectroscopic techniques were employed for the experimental study. Density functional theoretical calculations were performed to find the relative population of the conformers. The calculations predict that, with increase in temperature, the population of trans-enol increases, while that of cis-enol decreases. At all temperatures, the population ratio of cis-enol to trans-enol increases in the order HPIP-c &lt; HPIP-b &lt; HPBI. Except for HPBI in methanol and ethylene glycol, the fluorescence of both emissions decreases with an increase in temperature and is more pronounced in the tautomer band than in the normal band. The data are analyzed using the Arrhenius and van’t Hoff equations. The change in the fluorescence with temperature is governed by (i) the change in the relative population of conformers and (ii) the increase in non-radiative decay from the excited states. 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subjects Atomic and molecular physics
Benzimidazoles - chemistry
Decomposition
Density
Ethylene Glycol - chemistry
Exact sciences and technology
Fluorescence
Fluorescent Dyes - chemistry
Hydrogen Bonding
Imidazoles - chemistry
Isomerism
Mathematical analysis
Methanol - chemistry
Methyl alcohol
Molecular properties and interactions with photons
Molecular spectra
Nitrogen - chemistry
Physics
Polarity
Pyridines - chemistry
Spectrophotometry, Ultraviolet
Tautomers
Temperature
Thermodynamics
title Temperature Effect on Dual Fluorescence of 2‑(2′-Hydroxyphenyl)benzimidazole and Its Nitrogen Substituted Analogues
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