Pyrimidine based highly sensitive fluorescent receptor for Al3+ showing dual signalling mechanism

• Published in: Organic & biomolecular chemistry 2010-11, Vol.8 (21), p.4892-4897
• Main Authors: Upadhyay, K K, Kumar, Ajit
• Format: Article
• Language: English
• Subjects: Aldehydes - chemical synthesis; Aldehydes - chemistry; Aluminum - analysis; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Isomerism; Limit of Detection; Linear Models; Magnetic Resonance Spectroscopy; Schiff Bases - chemical synthesis; Schiff Bases - chemistry; Spectrometry, Fluorescence - methods; Spectrophotometry; Uracil - analogs & derivatives; Uracil - chemical synthesis; Uracil - chemistry
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c0ob00171f

A new fluorescent probe (5-[(4-diethylamino-2-hydroxy-benzylidene)-amino]-1H-pyrimidine-2, 4-dione) (Receptor 1) has been synthesized by the Schiff base condensation of 5-aminouracil with 4-(diethylamino)salicylaldehyde. The receptor 1 exhibits high selectively for Al(3+) in DMSO as well as in aqueous solution even in the presence of biologically relevant cations such as Na(+), K(+), Ca(2+), Mg(2+), Pb(2+) and several transition metal ions. The lowest detection limit for the receptor 1 was found to be 1.62 × 10(-10) M with its linear response towards Al(3+) in the concentration range of 1.75 × 10(-9) to 3.3 × 10(-8) M in DMSO. Receptor 1 is the first ever example where a single molecular probe is able to show imine (C=N) isomerization inhibition along with twisted intramolecular charge transfer (TICT) in combinatorial fashion.