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 xray 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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BibTeX
@article{marcoguimbao2026benzylic,
title = {{Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems}},
author = {Jorge Juan Marco‐guimbao and Eric Meichsner and Unai Calvo and Michel Holler and Béatrice Delavaux‐nicot and Jon M Matxain and Juan Luis Delgado and Jean‐françois Nierengarten and Iwona Nierengarten},
journal = {Chemistry - A European Journal},
year = {2026},
month = sep,
doi = {10.1002/chem.71754},
url = {https://hal.science/hal-05774834v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Benzylic Oxidation of Pillar[5]Arene: From Homo‐ to Cross‐Conjugated Macrocyclic Systems
AU - Jorge Juan Marco‐guimbao
AU - Eric Meichsner
AU - Unai Calvo
AU - Michel Holler
AU - Béatrice Delavaux‐nicot
AU - Jon M Matxain
AU - Juan Luis Delgado
AU - Jean‐françois Nierengarten
AU - Iwona Nierengarten
PY - 2026
DA - 2026/09/30
JO - Chemistry - A European Journal
DO - 10.1002/chem.71754
UR - https://hal.science/hal-05774834v1
AB - 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 xray 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.
SN - 0947-6539
SN - 1521-3765
ER -