Pillarenes are a pillar-shaped macrocycle constructed from electron-rich arenes covalently linked with methylene linker.  An internal cavity of pillararene is capable of encapsulating ranges of organic guests. In 2020, our group reported a rapid and efficient synthesis of pertosylated pillar[5]arene in excellent yield (>70%) in one-step. To further investigate into this macrocyclic motif, we prepared a novel macrocycle 1, Pillar[4]OTs[1]BQ, containing a benzoquinone unit within the structure. Macrocycle 1 possesses a thermo-responsive property in which the solution of 1 in organic solvent shows reversibly colour changes at different temperature. Post-synthetic modifications of 1 by SN2 reactions with pyridine gave an octa-cationic macrocyclic host which can improve water solubility and binding affinities towards anionic guest molecules in aqueous solution. In the future, tosylate-functionalised pillar[5]arene will be used a precursor in other applications such as sensing, recognition, extraction of target guest.

Synthesis of Tosylated Pillar[5]arene Derivatives and Applications in Chemical Extractions and Smart Sensors

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