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

Published online 2011-06-24

Benzopyrrole derivatives as effective anion receptors in highly competitive solvents

Janusz Jurczak1,2*, Michał J. Chmielewski1,2, Paweł Dydio1,2, Dawid Lichosyt1,2, 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.