Selective Extraction, Recovery, and Sensing of Hydroquinone Mediated by a Supramolecular Pillar[5]quinone Quinhydrone Charge-Transfer Complex.

Intermolecular interactions between an electron-rich aromatic hydroquinone (HQ) with its electron deficient counterpart, benzoquinone (BQ), result in the formation of a quinhydrone charge-transfer complex. Herein, we report a novel quinhydrone-type complex between pillar[5]quinone (P[5]Q) and HQ. Characterized by a suite of spectroscopic techniques including 1H NMR, UV-visible, and FTIR together with PXRD, SEM, BET, CV, and DFT modeling studies, the stability of the complex is determined to be due to an electron-proton transfer reaction coupled with a complementary donor-acceptor interaction. The selectivity of P[5]Q toward HQ over other dihydroxybenzene isomers allows for not only the naked-eye detection of HQ but also its selective liquid-liquid extraction and recovery from aqueous media.

Pertosylated pillar[5]arene: self-template assisted synthesis and supramolecular polymer formation.

A facile synthesis of decatosylate pillar[5]arene 1 is reported in excellent yield (>70%). The high yield is attributed to a self-template effect of the pendant tosylate arms. The X-ray crystal structure shows the formation of a linear supramolecular polymer, stabilised by intermolecular pillar[5]arene-tosylate inclusion complexes. These polymeric arrays persist in solution and form rod-like microfibril nanostructures evidenced by SEM.