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Paper | Regular issue | Vol 102, No. 1, 2021, pp.81-91
Published online, 18th November, 2020
DOI: 10.3987/COM-20-14363
■ Probing the Reaction of N,N-Dimethyformamide Dimethyl Acetal with p-tert-Butylthiacalix[4]arene Tetrahydrazides: A Facile Approach for the Synthesis and Application of Novel Metal Receptors

Omran A. Omran and Ayman Nafady*

*Chemistry Department, Faculty of Science, Sohag University, 82524, Sohag, Egypt

Abstract

Recent developments in the field of sensing and recognition revealed that artificial receptors based on calix[4]arenes with π-conjugated fluorophoric or chromophoric moieties are efficient in enhancing selectivity/sensitivity as well as the binding affinity for ionic or molecular recognition. Herein, via studying the reaction of dimethylformamide dimethyl acetal (DMF–DMA) with p-tert-butylthiacalix[4]arene tetrahydrazides in three different conformers (i.e., cone, partial-cone, and 1,3-alternate), the formation of novel lower rim p-tert-butylthiacalix[4]arene derivative (cone, partial-cone, and 1,3-alternate) conformers in high yields (80, 95, and 85%, respectively) was achieved. The structure of isolated products was confirmed using different spectroscopic and analytical techniques such as FT-IR, 1H NMR, 13C NMR, and elemental analysis. Importantly, the synthesized receptors showed preferential uptakes of alkali (Na+, K+ and Cs+), heavy (Pb2+, Cd2+, Hg2+, and Ag+) and transition (Ni2+, Co2+, and Cu2+) metal ions via liquid–liquid extraction method. The finding of this work adds new compounds to the growing family of thiacalix[4]arenes and validates their high sensitivity and selectivity in detection of heavy metal ions.