Development of tBu-phenyl Acetamide Appended Thiacalix[4]arene as “Turn-ON” Fluorescent Probe for Selective Recognition of Hg(II) Ions

Herein, a novel N-(4-(tert-butyl)-phenyl)-2-chloroacetamide functionalized thiacalix[4]arene architecture, viz TCAN2PA has been synthesized and the sensing behaviour towards metal ions were explored. The probe, TCAN2PA displayed “turn-on” fluorescence response towards Hg(II) ions in acetonitrile over a series of competing common metal ions. A bathochromic shift in absorption band along with a significant “Turn-On” fluorescence behaviour of TCAN2PA was observed upon interaction with Hg(II) ions. The lower rim modification of thiacalixarene with N-(4-(tert-butyl)-phenyl)-2-chloroacetamide actively contributes toward the fluorescence property due to the presence of strong electron-donating aryl amido substituent. Fluorescence titration experiments were conducted to find out the limit of detection and to understand binding stoichiometry as well. The electron transfer interactions between the electron rich TCAN2PA host with Hg(II) ions have been postulated which is also supported by computational modelling insights.