Excited State Intramolecular Proton Transfer in O-Tosylaminobenzaldehyde

Excited State Intramolecular Proton Transfer in O-Tosylaminobenzaldehyde

Excited state intramolecular proton transfer (ESIPT) in o-tosylaminobenzaldehyde has been investigated. According to quantum-chemical calculations ESIPT in o-tosylaminobenzaldehyde is barrierless. Product of ESIPT undergoes efficient nonradiative deactivation caused by internal rotation of C(H)OH-gr...

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Veröffentlicht in:Journal of fluorescence 2012-07, Vol.22 (4), p.1095-1100
Hauptverfasser: Khimich, Mikhail N., Popov, Leonid D., Burlov, Anatoly S., Uzhinov, Boris M.
Format: Artikel
Sprache:eng
Schlagworte:
Analytical Chemistry
Benzaldehydes - chemistry
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Electron Transport
Original Paper
Protons
Spectrometry, Fluorescence
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Zusammenfassung:Excited state intramolecular proton transfer (ESIPT) in o-tosylaminobenzaldehyde has been investigated. According to quantum-chemical calculations ESIPT in o-tosylaminobenzaldehyde is barrierless. Product of ESIPT undergoes efficient nonradiative deactivation caused by internal rotation of C(H)OH-group. The solvent orientational relaxation in anionic form of o-tosylaminobenzaldehyde was detected. The mechanism of anionic form fluorescence quenching at the addition of the base in a protic solvent is proposed. It consists in the intermolecular proton transfer from the protonated base to oxygen atom of aldehyde group followed by the internal rotation of C(H)OH-group.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-012-1048-y