Fluorescent organic nanoparticles of dihydropyrimidone derivatives for selective recognition of iodide using a displacement assay: application of the sensors in water and biological fluids

Abstract

Fluorescent organic nanoparticles (FON's) derived from dihydropyrimidone derivatives (1–4) were developed and evaluated for their sensor properties. Nano-aggregates of compound 3 and 4 resulted in sensors. Nano-aggregates of compound 3 showed enhancement in the monomer peaks of the pyrene moiety after the addition of mercury. Nano-aggregates of compound 4 resulted in quenching of intensity upon addition of Hg²⁺. On the other hand, no sensor activity was recorded for nano-aggregates of compounds 1 and 2. Further, the complex of nano-aggregates of 3 and mercury (3·Hg²⁺) recognised iodide ions by showing quenching in monomer and excimer emission with a detection limit of 0.2 nM in aqueous medium; however the resultant metal complex 4·Hg²⁺ does not show any anion sensing activity. Receptor 3·Hg²⁺ has a highly sensitive and selective response toward I⁻ ions. Therefore, the iodide content of tap water, urine and blood serum is monitored using this sensor and it is found that the sensor can detect a range of iodide in tap water, urine and blood serum. To the best of our knowledge, the system represents the first example of iodide recognition using FONs.