Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Jurczak, Janusz; Chmielewski, Michał J.; Dydio, Paweł; Lichosyt, Dawid; Ulatowski, Filip; Zieliński, Tomasz

doi:10.1351/PAC-CON-10-11-11

Pure Appl. Chem., 2011, Vol. 83, No. 8, pp. 1543-1554

http://dx.doi.org/10.1351/PAC-CON-10-11-11

Published online 2011-06-24

Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Janusz Jurczak^1,2*, Michał J. Chmielewski^1,2, Paweł Dydio^1,2, Dawid Lichosyt^1,2, Filip Ulatowski² and Tomasz Zieliński²

¹ Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
² Institute of Organic Chemistry, Polish Academy of Sciences Kasprzaka 44/52, 01‑224 Warsaw, Poland

Abstract: Neutral anion receptors working in highly demanding solvents are new materials being sought. Benzopyrroles are more acidic than amides and pyrrole itself, and are promising building blocks in the design of host compounds. A whole series of receptors based upon benzopyrroles were synthesized and evaluated. They include carbazole, dipyrrolonaph-thalene, and 7-aminoindole-based hosts. Most of them demonstrate moderate binding affinities in dimethyl sulfoxide (DMSO) and have good selectivity toward tetrahedral oxyanions. Recently, a group of receptors utilizing 7-aminoindole and urea moieties proved to work in a very competitive solvent—methanol.