Solvent interactions with the indole chromophore

Tatischeff, Irène; Klein, Roger A.; Zemb, Thomas; Duquesne, M.

doi:10.1016/0009-2614(78)80127-4

Cited by 37 publications

(17 citation statements)

References 25 publications

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“…The fluorescence band of indole derivatives is solvent dependent, being less structurated and red shifted in polar solvents (De Lauder and Wahl, 1971;Tatischeff et al, 1978;Santus et al, 1980). These characteristics have been extensively employed to infer the indole moiety microenvironment (Turro et af., 1980, Encinas andLissi, 1985;Lissi et al, 1990).…”

Section: Fluorescence Band Position and Lifetimesmentioning

confidence: 99%

PHOTOPHYSICAL STUDIES OF INDOLE ALKANOIC ACIDS and TRYPTAMINE IN REVERSE MICELLES OF SODIUM DIOCTYL SULFOSUCCINATE

Encinas

Lissi

Bertolotti

et al. 1990

Photochem & Photobiology

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Abstract— The fluorescence spectra and emission lifetimes of several 3‐alkanoic indoles of different chain length and tryptamine (TA) were studied in sodium dioctyl sulfosuccinate (AOT)/heptane reverse micelles over a wide range of water/AOT ratio (R ‐ 5 to 44). Fluorescence quenching experiments were done using carbon tetrachloride and acrylamide as quenchers. Experiments with TA were carried out using water at pH 3 in order to assure its protonation. Under these conditions, the results indicate that the indole moiety of TA remains at the micellar interface over all the range considered. Furthermore, the results can be interpreted assuming for the TA population a single microenvironment whose properties remain almost invariant when R increases from 11 to 44. The studies employing the 3‐alkanoic indoles were carried out at pH 10. Under these conditions, the anions are progressively displaced to the water pool when the R value increases. This displacement is determined by the length of the side alkyl chain of the 3‐indole derivatives. For these compounds, the quenching experiments indicate that, even at low R values, the excited indole moieties are distributed among different microenvironments.

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Section: Fluorescence Band Position and Lifetimesmentioning

confidence: 99%

PHOTOPHYSICAL STUDIES OF INDOLE ALKANOIC ACIDS and TRYPTAMINE IN REVERSE MICELLES OF SODIUM DIOCTYL SULFOSUCCINATE

Encinas

Lissi

Bertolotti

et al. 1990

Photochem & Photobiology

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“…In the vapor phase the 'Li, excited state is lowest in energy for most indole derivatives, but in polar solvents, the 'La excited state is preferentially stabilized and the latter becomes the lowest excited singlet state (8)(9)(10)(11)(12). In the vapor phase the 'Li, excited state is lowest in energy for most indole derivatives, but in polar solvents, the 'La excited state is preferentially stabilized and the latter becomes the lowest excited singlet state (8)(9)(10)(11)(12).…”

Section: Introductionmentioning

confidence: 98%

Photophysics of indole derivatives: experimental resolution of L a and L b transitions and comparison with theory

et al. 1990

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Fluorescence excitation and anisotropy spectra are presented for a set of methyl and methoxyindoles at -50°C in propylene glycol glass. These spectra are interpreted in terms of two overlapping i-i electronic transitions ('La and 'L). Semiempirical molecular orbital calculations are presented to correlate with the observed spectral changes caused by methyl and methoxy substitution. occupied MO's (HOMO's) to the 14 lowest unoccupied MO's (LUMO's) using Mataga-Nishimoto (MN) electron repulsion integrals, hereafter referred to as the SCI

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“…[1][2][3] Large solvent effects on the emission maximum are due to the presence of two overlapping electronic transitions with different polarity in the first absorption band, whose relative energy depends on solvent polarity and solvent relaxation. [3][4][5][6][7][8][9][10][11] The indole chromophore has multiple nonradiative decay pathways that depend on environment. A complex fluorescence decay is usually observed for single tryptophan in proteins, [1][2][3][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] peptides, 29 -34 as a free amino acid or its derivatives or analogues.…”

Section: Introductionmentioning

confidence: 99%

Influence of solvents and leucine configuration at position 5 on tryptophan fluorescence in cyclic enkephalin analogues

et al. 2001

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Solvent interactions with the indole chromophore

Cited by 37 publications

References 25 publications

PHOTOPHYSICAL STUDIES OF INDOLE ALKANOIC ACIDS and TRYPTAMINE IN REVERSE MICELLES OF SODIUM DIOCTYL SULFOSUCCINATE

PHOTOPHYSICAL STUDIES OF INDOLE ALKANOIC ACIDS and TRYPTAMINE IN REVERSE MICELLES OF SODIUM DIOCTYL SULFOSUCCINATE

Photophysics of indole derivatives: experimental resolution of L a and L b transitions and comparison with theory

Influence of solvents and leucine configuration at position 5 on tryptophan fluorescence in cyclic enkephalin analogues

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