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Excited‐State Intramolecular Proton Transfer: Photoswitching in Salicylidene Methylamine Derivatives
Author(s) -
Jankowska Joanna,
Rode Michał F.,
Sadlej Joanna,
Sobolewski Andrzej L.
Publication year - 2014
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201301205
Subject(s) - methylamine , chemistry , intramolecular force , ab initio , singlet state , excited state , electron transfer , molecule , ground state , computational chemistry , intersystem crossing , proton , photochemistry , stereochemistry , atomic physics , organic chemistry , physics , quantum mechanics
The effect of chemical substitutions on the photophysical properties of the salicylidene methylamine molecule (SMA) (J. Jankowska, M. F. Rode, J. Sadlej, A. L. Sobolewski, ChemPhysChem , 2012 , 13 , 4287–4294) is studied with the aid of ab initio electronic structure methods. It is shown that combining π‐electron‐donating and π‐electron‐withdrawing substituents results in an electron‐density push‐and‐pull effect on the energetic landscape of the ground and the lowest excited ππ* and n π* singlet states of the system. The presented search for the most appropriate SMA derivatives with respect to their photoswitching functionality offers an efficient prescreening tool for finding chemical structures before real synthetic realization.