Synthesis, structure and coordination properties of novel bifunctional carboxylic derivatives of 1,3-alternate tetrathiacalix[4]arene

Abstract

New bifunctional derivatives of 1,3-alternate tetrathiacalix[4]arene decorated with carboxylic, ester, hydrazide and/or hydrazone groups have been synthesized with good yields using the tetrathiacalix[4]arene derivatives with incorporated pairs of carboxylic and ester groups as versatile building blocks. The structural peculiarities of the obtained bifunctional compounds have been investigated by means of X-ray analysis, IR and NMR spectroscopy. The recognition ability of the synthesized macrocycles towards some alkali, alkali-earth and transition metal ions has been investigated applying a solvent extraction method. The results showed that the structure of a calix[4]arene platform as well as the nature of functional substitutes located on opposite sides of the macrocycle are critical for the coordination properties of the synthesized compounds.