Excited State Intramolecular Proton Transfer in O-Tosylaminobenzaldehyde
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- Khimich, M.N., Popov, L.D., Burlov, A.S. et al. J Fluoresc (2012) 22: 1095. doi:10.1007/s10895-012-1048-y
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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.