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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

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

by
Paolo Della Sala
1,*,
Veronica Iuliano
1,
Margherita De Rosa
1,
Carmen Talotta
1,
Rocco Del Regno
1,
Placido Neri
1,
Silvano Geremia
2,*,
Neal Hickey
2 and
Carmine Gaeta
1
1
Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia “A. Zambelli”, Università degli Studi di Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, SA, Italy
2
Centro di Eccellenza in Biocristallografia, Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(17), 4142; https://doi.org/10.3390/molecules29174142
Submission received: 2 August 2024 / Revised: 23 August 2024 / Accepted: 27 August 2024 / Published: 31 August 2024
(This article belongs to the Special Issue Exclusive Contributions by the Editorial Board Members (EBMs) of the Organic Chemistry Section of Molecules)
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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.
Keywords: deep-cavity hosts; hybrid macrocycles; fragment coupling synthesis deep-cavity hosts; hybrid macrocycles; fragment coupling synthesis

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MDPI and ACS Style

Della Sala, P.; Iuliano, V.; De Rosa, M.; Talotta, C.; Del Regno, R.; Neri, P.; Geremia, S.; Hickey, N.; Gaeta, C. Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures. Molecules 2024, 29, 4142. https://doi.org/10.3390/molecules29174142

AMA Style

Della Sala P, Iuliano V, De Rosa M, Talotta C, Del Regno R, Neri P, Geremia S, Hickey N, Gaeta C. Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures. Molecules. 2024; 29(17):4142. https://doi.org/10.3390/molecules29174142

Chicago/Turabian Style

Della Sala, Paolo, Veronica Iuliano, Margherita De Rosa, Carmen Talotta, Rocco Del Regno, Placido Neri, Silvano Geremia, Neal Hickey, and Carmine Gaeta. 2024. "Deep-Cavity Calix[4]naphth[4]arene Macrocycles: Synthesis, Conformational Features, and Solid-State Structures" Molecules 29, no. 17: 4142. https://doi.org/10.3390/molecules29174142

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