The 4-amino-1,8-naphthalimide-based anion receptor 3 binds dihydrogenphosphate with 1:1 stoichiometry through cooperative hydrogen bonding to a naphthalimide N–H and thiourea N–H groups. This was clearly established from 1H NMR titration experiments in DMSO-d6 where a substantial shift in the resonance for the naphthalimide N–H was observed concomitant with the expected thiourea N–H chemical shift migration upon successive additions of H2PO4−. However, whilst 1H NMR titration experiments indicate that 3 was capable of binding other anions such as acetate, the naphthalimide N–H does not participate and the N–H resonance was essentially invariant during the titration. The lack of cooperative binding in this instance was justifiable on steric grounds.
Available online 9 August 2005.
Field of Research
030302 Nanochemistry and Supramolecular Chemistry
Socio Economic Objective
970103 Expanding Knowledge in the Chemical Sciences
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