Inter- and intramolecular excited state proton transfer in 2-hydroxy-9H-carzole-1-carboxylic acid

Absorption, fluorescence and fluorescence excitation spectroscopy and single photon counting time dependence spectrofluorimetry have been used to study the inter- and intramolecular excited state proton transfer (ESIPT) reactions in 2-hydroxy-9H-carbazole-1-carboxylic acid (2-HCA). Except in cyclohe...

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Bibliographic Details
Published in:Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2005-04, Vol.61 (6), p.1247-1257
Main Authors: Nayak, M.K., Dogra, S.K.
Format: Article
Language:English
Subjects:
2-Hydroxy-9H-carbazole-1-carboxylic acid, Absorption spectrum
Carbazoles - chemistry
Carboxylic Acids - chemistry
Excited state proton transfer
Fluorescence spectrum
Hydrogen-Ion Concentration
Protons
Prototropic equilibria
Solubility
Solvents - chemistry
Spectrometry, Fluorescence
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Summary:Absorption, fluorescence and fluorescence excitation spectroscopy and single photon counting time dependence spectrofluorimetry have been used to study the inter- and intramolecular excited state proton transfer (ESIPT) reactions in 2-hydroxy-9H-carbazole-1-carboxylic acid (2-HCA). Except in cyclohexane and water (pH 5) dual fluorescence is observed in rest of the solvents used. Normal Stokes shifted band seems to originate from 2-HCA-1-c and tautomer emission band from the tautomer formed by ESIPT in 2-HCA-1-c followed by structural reorganization. Both these emission band systems originate from the same ground state species. AM1 and CNDO/S-CI calculations have been carried out to establish the identity of the species. Different prototropic equilibria have been determined and discussed.
ISSN:1386-1425
DOI:10.1016/j.saa.2004.06.049