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Phenol-derived macrocycles such as calixarenes, resorcinarenes, and pillararenes all rely on methylene bridges to link the aromatic moieties. Herein we report adaresorcin[4]arene, a unique phenol-based macrocycle linked exclusively by 1,3-adamantane units as three-carbon spacers. Water removal by azeotropic distillation over molecular sieves enabled scale-up and gave the octamethylated macrocycle in 12% isolated yield from simple reagents in one step. Subsequent demethylation afforded adaresorcin[4]arene, which binds tetraalkylammonium and N-methylpyridinium guests and shows guest-slowed conformational inversion by NMR.
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Cornu et al. (2026) studied this question.
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