Journal of Fluorescence

, Volume 22, Issue 4, pp 1095–1100

Excited State Intramolecular Proton Transfer in O-Tosylaminobenzaldehyde

  • Mikhail N. Khimich
  • Leonid D. Popov
  • Anatoly S. Burlov
  • Boris M. Uzhinov
Original Paper

DOI: 10.1007/s10895-012-1048-y

Cite this article as:
Khimich, M.N., Popov, L.D., Burlov, A.S. et al. J Fluoresc (2012) 22: 1095. doi:10.1007/s10895-012-1048-y

Abstract

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.

Keywords

Fluorescence Proton transfer Internal rotation Relaxation 

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Mikhail N. Khimich
    • 1
  • Leonid D. Popov
    • 2
  • Anatoly S. Burlov
    • 3
  • Boris M. Uzhinov
    • 1
  1. 1.Chemistry DepartmentMoscow State UniversityMoscowRussia
  2. 2.Chemistry DepartmentSouthern Federal UniversityRostov-on-DonRussia
  3. 3.Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia

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