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

Autor:	Della Sala, Paolo, Iuliano, Veronica, De Rosa, Margherita, Talotta, Carmen, Del Regno, Rocco, Neri, Placido, Geremia, Silvano, Hickey, Neal, Gaeta, Carmine
Předmět:	CONFORMATIONAL analysis HYDROGEN bonding AROMATIC compounds NAPHTHALENE PHENOL
Zdroj:	Molecules; Sep2024, Vol. 29 Issue 17, p4142, 14p
Abstrakt:	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 (C4N4) and its permethylated analog (C4N4-Me), thereby expanding the calix[n]naphth[m]arene family. C4N4 was synthesized through a 2 + 2 fragment coupling macrocyclization under acidic conditions, where the solvent played a crucial role in selectively forming the C4N4 derivative. The X-ray structure of C4N4 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 C4N4-Me exhibits a 1,3,5,7-alternate conformation. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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