Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures.

We recently introduced calix[]naphth[]arenes as a novel class of deep-cavity hybrid macrocycles constituted by phenol (n) and naphthalene (m) units. In this study, we report the synthesis, conformational analysis, spectroscopic properties, and solid-state structures of calix[4]naphth[4]arene () and its permethylated analog (), thereby expanding the calix[]naphth[]arene family. was synthesized through a 2 + 2 fragment coupling macrocyclization under acidic conditions, where the solvent played a crucial role in selectively forming the derivative.

Thermodynamically Templated Macrocyclizations: Enhancing the Synthesis of Prism[5]arenes with Tailor-Made Guests.

The macrocyclization of 2,6-dialkoxynaphthalene monomers to prism[5]arenes is thermodynamically templated by DABCO cations. In this study, we demonstrate that a greater template affinity for prism[5]arene improves the macrocyclization yield. By using novel templating cations, the yield of alkoxy-prism[5]arenes increases significantly compared with those of previously reported procedures, while the purification process becomes easier and faster.

Under the Influence of Water: Molecular Recognition of Organic Hydrophilic Molecules in Water with a Prismarene Host Driven by Hydration Effects.

A water-soluble prism[5]arene host can form endo-cavity complexes with hydrophilic organic substances in water by displacing frustrated water molecules from its deep cavity. Water molecules structured at both rims of the prismarene host can mediate hydrogen bonding interactions with the guest. Water-mediated hydrogen bonding interactions were invoked here to elucidate the elevated binding affinities and selectivity of the prismarene host toward hydrophilic organic guests.

The Resorcinarene Hexameric Capsule as a Supramolecular Photoacid to Trigger Olefin Hydroarylation in Confined Space.

The self-assembled resorcinarene capsule C shows remarkable photoacidity upon light irradiation, which is here exploited to catalyze olefin hydroarylation reactions in confined space. An experimental pKa* value range of -3.3--2.

Insights into the Friedel-Crafts Benzoylation of -Methylpyrrole inside the Confined Space of the Self-Assembled Resorcinarene Capsule.

Friedel-Crafts benzoylation of -methylpyrrole can run inside the confined space of the hexameric resorcinarene capsule . The bridged water molecules at the corner of act as H-bonding donor groups to polarize the C-Cl bond of benzoyl chlorides -. Confinement effects on the regiochemistry of the FC benzoylation of -methylpyrrole are observed.