Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures-Reference-Cited by-同舟云学术

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

Published:2024-08-31 Issue:17 Volume:29 Page:4142
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Della Sala Paolo¹^ORCID,Iuliano Veronica¹^ORCID,De Rosa Margherita¹^ORCID,Talotta Carmen¹^ORCID,Del Regno Rocco¹^ORCID,Neri Placido¹^ORCID,Geremia Silvano²^ORCID,Hickey Neal²^ORCID,Gaeta Carmine¹^ORCID

Affiliation:

1. Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia “A. Zambelli”, Università degli Studi di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy

2. Centro di Eccellenza in Biocristallografia, Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy

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 (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.

Funder

Ministero dell’Università e della Ricerca

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/17/4142/pdf

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