1. Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures.
- Author
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Della Sala P, Iuliano V, De Rosa M, Talotta C, Del Regno R, Neri P, Geremia S, Hickey N, and Gaeta C
- Abstract
We recently introduced calix[ n ]naphth[ m ]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 ( C
4 N4 ) and its permethylated analog ( C4 N4 -Me ), thereby expanding the calix[ n ]naphth[ m ]arene family. C4 N4 was synthesized through a 2 + 2 fragment coupling macrocyclization under acidic conditions, where the solvent played a crucial role in selectively forming the C4 N4 derivative. The X-ray structure of C4 N4 reveals a chair-like 1,2,3,4-alternate conformation characterized by two opposing 3/4-cone moieties stabilized by intramolecular hydrogen bonds. In contrast, the X-ray structure of C4 N4 -Me exhibits a 1,3,5,7-alternate conformation.- Published
- 2024
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