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Access to highly strained molecules remains a challenge. We report the synthesis of a bench-stable and highly strained (∼135 kcal mol⁻¹) deep cavitand. 

Herein, we present 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as an efficient solvent for synthesizing resorcin[n]arenes in the presence of catalytic amounts of HCl at ambient temperature and within minutes. Remarkably, resorcinols with electron-withdrawing groups and halogens, which are reported in the literature as the most challenging precursors in this cyclization, are tolerated. This method leads to a variety of 2-substituted resorcin[n]arenes in a single synthetic step with isolated yields up to 98%. 

Abstract Herein, we report the synthesis of a new series of rigid, allmeta‐phenylene, conjugated deep‐cavity molecules, displaying high binding affinity towards buckyballs. A facile synthetic approach with an overall combined yield of approximately 53% in the last two steps has been developed using a templating strategy that combines the general structure of resorcin[4]arene and [12]cyclo‐meta‐phenylene. These two moieties are covalently linked via four acetal bonds, resulting in a glove‐like architecture.¹H NMR titration experiments reveal fullerene binding affinities (K_a) exceeding ≥10⁶ M⁻¹. The size complementarity between fullerenes and these scaffolds maximizes CH⋯π and π⋯π interactions, and their host:guest adduct resembles a ball in a glove, hence their name as nanogloves. Fullerene recognition is tested by suspending carbon soot in a solution of nanoglove in 1,1,2,2‐tetrachloroethane, where more than a dozen fullerenes are observed, ranging from C₆₀to C₉₆.