A new family of bis-ureidic receptors for pyrophosphate optical sensing

A new family of bis-ureidic receptors (L(1)-L(6)) has been synthesised. The binding properties of L(1)-L(6) towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of (1)H-NMR, UV-Vis and fl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2013-04, Vol.11 (15), p.2445-2451
Main Authors: Caltagirone, Claudia, Bazzicalupi, Carla, Isaia, Francesco, Light, Mark E, Lippolis, Vito, Montis, Riccardo, Murgia, Sergio, Olivari, Martina, Picci, Giacomo
Format: Article
Language:English
Subjects:
Chemistry Techniques, Analytical - instrumentation
Diphosphates - analysis
Diphosphates - chemistry
Models, Molecular
Molecular Conformation
Optical Phenomena
Urea - chemistry
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Summary:A new family of bis-ureidic receptors (L(1)-L(6)) has been synthesised. The binding properties of L(1)-L(6) towards different anions (acetate, benzoate, glutarate, malonate, dihydrogen phosphate, hydrogen pyrophosphate, triphosphate, AMP and ADP) have been studied by means of (1)H-NMR, UV-Vis and fluorescence spectroscopies and a remarkable affinity for HPpi(3-) has been observed in the case L(3) (in DMSO-d6 and DMSO-d6-5% H2O) which also acts as a fluorimetric chemosensor, even to the naked eye, for this anion. Theoretical calculations helped us explain the binding properties observed.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob27244c