Three aminonaphthalimide derivatives were synthesized bearing different anchoring groups in their 4-position in order to adjust the supramolecular interactions with carboxylato-pillararene (WP5), an anionic, water-soluble host. The modification of the anchor groups resulted in varying association constants embracing three orders of magnitude (Ka from ∼103 to ∼106) in buffered water. Since the fluorophore responded significantly to the electronic environment, large fluorescence quenching was observed with the anionic WP5 host. The naphthalimide indicator-WP5 supramolecular assemblies were used to detect arginine and lysine with complete selectivity over other non-basic α-amino acids by turn-on fluorescence. The same assemblies proved to be highly sensitive fluorescence displacement assays for the detection of cadaverine.
ASJC Scopus subject areas
- Chemical Engineering(all)