ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Fluoride anion sensing using colorimetric reagents containing binaphthyl moiety and urea binding site
Roman Mikláš, Peter Kasák, Ferdinand Devínsky, and Martin Putala
Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius Uviversity, Odbojárov 10, 832 32 Bratislava, Slovakia
Received: 16 January 2009 Revised: 17 June 2009 Accepted: 18 June 2009
Abstract: Four 1,1′-binaphthalene based bis-urea derivatives bearing aryl groups at end-on nitrogen atoms IIIa–d were synthesized as potential sensor molecules. These receptors show characteristic UV-VIS spectral changes on complexation
with anions and they exhibit selective recognition of F− over other halide anions. Interaction of a fluoride anion with urea NH groups was confirmed by 1H NMR data. The presence of an electron-withdrawing nitro group in N′-aryls (receptors IIIa and IIIb) appeared to be necessary for naked-eye colorimetric detection. These receptors show dramatic color change from light-yellow
to orange (IIIa) or to orange-red (IIIb) in the presence of guest fluoride anions already at concentrations of 10−5 mol dm−3 of the receptor and host.
Keywords: 1,1′-binaphthalene - binaphthyl - chromogenic anion receptor - urea
Full paper is available at www.springerlink.com.
Chemical Papers 63 (6) 709–715 (2009)
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