Excited-state intramolecular proton transfer: photoswitching in salicylidene methylamine derivatives.
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 nπ* 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.
College of Interfaculty Individual Studies in Mathematics and Natural Sciences, University of Warsaw, Żwirki i Wigury 93, 02-089 Warsaw (Poland); Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw (Poland), Fax: (+48) 22 822 59 96.
Joanna
J
Jankowska
Michał F
MF
Rode
Joanna
J
Sadlej
Andrzej L
AL
Sobolewski
ab initio calculations; conical intersection; molecular photoswitch; proton transfer; schiff bases