Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure water

CASULA, ARIANNA;Bazzicalupi, Carla;BETTOSCHI, ALEXANDRE;CADONI, ENZO;Coles, Simon J.;Horton, Peter N.;ISAIA, FRANCESCO;LIPPOLIS, VITO;Mapp, Lucy K.;Marini, Giada M.;MONTIS, RICCARDO;SCORCIAPINO, MARIANO ANDREA;CALTAGIRONE, CLAUDIA

2016-01-01

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Abstract

Three fluorescent asymmetric bis-urea receptors (L1-L3) have been synthesised. The binding properties of L1-L3 towards different anions (fluoride, acetate, hydrogencarbonate, dihydrogen phosphate, and hydrogen pyrophosphate HPpi3-) have been studied by means of 1H-NMR, UV-Vis and fluorescence spectroscopy, single crystal X-ray diffraction, and theoretical calculations. In particular, a remarkable affinity for HPpi3- has been observed in the case L1 (DMSO-d6/0.5% H2O) which also acts as a fluorimetric chemosensor for this anion. Interestingly, when L1 is included in cetyltrimethylammonium (CTAB) micelles, hydrogen pyrophosphate recognition can also be achieved in pure water.