International Summer School PROGRAM - Laboratoire d'Infochimie ...

NOVEL PHOTORESPONSIBLE ANION RECEPTORS
Kajetan Dąbrowa a , Patryk Niedbała a,b , Janusz Jurczak a,b
a) Institute of Organic Chemistry PAS, Kasprzaka 44/52, 01-224 Warsaw
b)
The Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw
kajetan.dabrowa@icho.edu.pl
Coordination chemistry of anions is one of the most vivid fields of supramolecular
chemistry, since anions are essential components of biological systems. [1]
Despite the observed rapid development in this area over the past two decades only a
small number of neutral receptors capable of selective binding in demanding solvents
was developed. [2]
There are known only several methods of modifying the binding properties of
artificial anions receptors, i.e. changing pH, redox reactions and irradiation by light. The
latter is the most interest and promising since it does not influence the charge of the
receptor – it may remain neutral. After the absorption of light the geometry of receptor
undergoes profound and reversible changes. So far there are only few examples of the
use of light as a factor triggering the change of receptors affinity toward anions. [3]
To fill this gap we synthesized and examined binding properties of neutral receptor of
type 1 (a - para, b - meta substitution), which undergo reversible E-Z isomerization
process controlled by light.
Receptors E-1a-b and Z-1a-b show a significant change in affinity for anions in
highly demanding solvent (DMSO-water mixtures). The best E/Z selectivity was
achieved for carboxylate anions.
[1] Gale, P. A., Chem. Soc. Rev., 2010, 39, 3746-3771, 10.1039/c001871f;
[2] P. A. Gale, S.E. Garcı´a-Garrido, J. Garric, Chem. Soc. Rev., 2008, 37, 151–190, 10.1039/B715825D
[3] Wang Y.,Bie F., Jiang H., Org. Lett., 2010, 12 (16), 3630–3633, DOI: 10.1021/ol1014043