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Photophysical properties of 2,3,6,7-tetrahydro-8-hydroxy-1H, 5H-benz[i, j] quinolizine-9-carboxaldehyde: Evidence of excited state intramolecular proton transfer but not of intramolecular charge transfer process

Paper ID Volume ID Publish Year Pages File Format Full-Text
29138 44124 2008 12 PDF Available
Title
Photophysical properties of 2,3,6,7-tetrahydro-8-hydroxy-1H, 5H-benz[i, j] quinolizine-9-carboxaldehyde: Evidence of excited state intramolecular proton transfer but not of intramolecular charge transfer process
Abstract

The photophysical behaviours of 2,3,6,7-tetrahydro-8-hydroxy-1H, 5H-benzo[i, j] quinolizine-9-carboxaldehyde (THBQC), a molecule having both the intramolecular excited state donor acceptor charge transfer and six member intramolecular hydrogen bonded proton transfer sites, have been investigated by steady state and time resolved spectroscopy in combination with quantum chemical calculations. The observed spectral characteristics of THBQC with variation of solvent properties, pH and temperature of the medium confirm the existence of different neutral and ionic species in the ground and excited states. Comparatively less solvent polarity dependent red shifted emission band of THBQC in all solvents is attributed to excited state intramolecular proton transfer of the closed conformer leading to keto-enol tautomerism but not of intramolecular charge transfer process. In polar solvents, apart from the proton transfer emission band, another band at higher energy region is attributed to the emission from the open solvated form. Evaluation of the potential energy surfaces by quantum chemical calculations using Density functional theory (DFT) and Hartree–Fock (HF) levels point towards the possibility of proton transfer reaction in the first excited state and correlate well with the experimental findings.

Keywords
2,3,6,7-Tetrahydro-8-hydroxy-1H, 5H-benzo[i, j] quinolizine-9-carboxaldehyde (THBQC); Excited state proton transfer (ESIPT); Keto-enol tautomerism; Fluorescence; Density functional theory
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Photophysical properties of 2,3,6,7-tetrahydro-8-hydroxy-1H, 5H-benz[i, j] quinolizine-9-carboxaldehyde: Evidence of excited state intramolecular proton transfer but not of intramolecular charge transfer process
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 197, Issue 1, 10 June 2008, Pages 62–73
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us