Synthesis of new anthracene-conjugated calix[4]arene as highly selective fluorescent chemosensor for determination of CN− ion

Abstract

A new calix[4]arene derivative substituted with anthracene at its 1,3-distal position was synthesized via a simple Schiff base reaction, and its structure was fully characterized by using ATR-FTIR, 1H-NMR, 13C-NMR, ESI-MS and elemental analysis techniques. Furthermore, the ion binding feature of the anthracene substituted calix[4]arene (Ant-Calix) was evaluated against Br−, Cl−, F−, HSO4−, NO3− and CN− ions. Various aspects of anion sensing phenomena were deeply assessed, and the findings addressed that Ant-Calix exhibited excellent selectivity for CN− and could detect in a very low detection limit 92.4 nM. Beside, when CN− ion was bound to the probe Ant-Calix, a significant color change from light green to pink color was observed under UV light. The fluorescence data was also employed to calculate the binding stoichiometry and association constant of the complex obtained between Ant-Calix and cyanide ion. In addition, the 1H-NMR technique was also used to elucidate the mechanism of the complex formation between Ant-Calix and CN−.