Closed Aromatic Tubes—Capsularenes

In this study, we describe a synthetic method for incorporating arenes into closed tubes that name capsularenes. First, prepared vase-shaped molecular baskets 4–7. The comprise benzene base fused to three bicycle[2.2.1]heptane rings extend phthalimide (4), naphthalimide (6), and anthraceneimide sides (7), each carrying dimethoxyethane acetal group. the presence of catalytic trifluoroacetic acid (TFA), acetals at top 4, 6 7 change aliphatic aldehydes followed by their intramolecular cyclization 1,3,5-trioxane (1H NMR spectroscopy). Such ring closure is nearly quantitative process furnishes differently sized capsularenes 1 (0.7×0.9 nm), 8 (0.7×1.1 nm;) 9 (0.7×1.4 characterized X-Ray crystallography, microcrystal electron diffraction, UV/Vis, fluorescence, cyclic voltammetry, thermogravimetry. With exceptional rigidity, unique topology, great thermal stability, perhaps tuneable optoelectronic characteristics, hold promise construction novel organic electronic devices.