Abstract
The anthryl-functionalized open-chain polyaza-alkanes L1, L2, and L3 have been synthesized, and their activity as fluorescent chemosensors has been studied in MeCN/H2O 70 : 30 (v/v) and H2O at 25° against the anions bromide, phosphate, sulfate, ATP, ADP, and GMP. The crystal structure of L3 has been solved by single-crystal X-ray-diffraction techniques. The emission intensity of L1 and L2 is selectively quenched in the presence of ATP at acidic pH in MeCN/H2O 70 : 30 (v/v). In H2O, the emission intensity of L1 and L2 is enhanced at neutral pH in the presence of ADP and ATP. The sensing behavior is discussed in terms of H-bonding or electrostatic anion-cation interactions. Receptor L3 does not show any significant change in fluorescence emission upon addition of anions. Protonation constants of the three ligands and stability constants of L2 with phosphate and sulfate were determined by potentiometric titration in MeCN/H2O. The stability constants obtained are compared with those obtained for the interaction of these anions with related open-chain polyamines.
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