Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems

ABSTRACT Selective benzylic oxidations of pillar[5]arene have been carried out to generate all the possible oxidized derivatives containing from one up to five carbonyl subunits. By using a mild oxidizing agent, namely DDQ, the conditions have been optimized to preferentially generate the monoketone derivative. The corresponding polyketones have been obtained by oxidation of the pillar[5]arene with SeO 2 under microwave irradiation. Six out of the seven oxidation products have been characterized by x‐ray crystal structure analysis. Effects resulting from the homo‐ and the cross‐conjugation within this series of compounds have been investigated and analyzed with the help of DFT calculations. Finally, binding studies have been also carried out with the pillar[5]arene and the pentaketone derivative in order to evaluate the effect of the C═O subunits on the affinity of the macrocyclic system for guest molecules.

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Publication Details

Journal
Chemistry - A European Journal
Published
2026-09-30
DOI
https://doi.org/10.1002/chem.71754
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
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Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems

Jon Mattin Matxain, Michel Holler, Juan Luis Delgado, Béatrice Delavaux‐Nicot et al.
Chemistry - A European Journal
Synthesis and Properties of Aromatic Compounds
article

Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems

Jon Mattin Matxain, Michel Holler, Juan Luis Delgado, Béatrice Delavaux‐Nicot, Unai Calvo, Eric Meichsner, Jean‐François Nierengarten, Iwona Nierengarten, Jorge Marco-Guimbao
article en

Abstract

ABSTRACT Selective benzylic oxidations of pillar[5]arene have been carried out to generate all the possible oxidized derivatives containing from one up to five carbonyl subunits. By using a mild oxidizing agent, namely DDQ, the conditions have been optimized to preferentially generate the monoketone derivative. The corresponding polyketones have been obtained by oxidation of the pillar[5]arene with SeO 2 under microwave irradiation. Six out of the seven oxidation products have been characterized by x‐ray crystal structure analysis. Effects resulting from the homo‐ and the cross‐conjugation within this series of compounds have been investigated and analyzed with the help of DFT calculations. Finally, binding studies have been also carried out with the pillar[5]arene and the pentaketone derivative in order to evaluate the effect of the C═O subunits on the affinity of the macrocyclic system for guest molecules.

Chemistry - A European Journal
Ikerbasque (ES), Centre National de la Recherche Scientifique (FR), Université Fédérale de Toulouse Midi-Pyrénées (FR), Polymat (ES), Laboratoire de Chimie de Coordination (FR), Institut de Physique et Chimie des Matériaux de Strasbourg (FR), Donostia International Physics Center (ES)
Clean water and sanitation
Openalex Percentile: Top 23%
Synthesis and Properties of Aromatic Compounds
DOIOpen Access PDFOpenAlex
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Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems — Jon Mattin Matxain, Michel Holler, et al. · Chemistry - A European Journal (2026) | TGRS Research Map | TGRS