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Triple Stack of a Viologen Derivative in a CB[10] Pair

Authors :
Olivier Ouari
Valérie Monnier
David Bardelang
Didier Gigmes
Simin Liu
Roselyne Rosas
Christophe Bucher
Laurence Charles
Hakim Karoui
Shagor Chowdhury
Anthony Kermagoret
Floris Chevallier
Fengbo Liu
The State Key Laboratory of Refractories and Metallurgy, School of Materials and Metallurgy, Wuhan University of Science and Technology, Wuhan 430081, People’s Republic of China
Laboratoire de Chimie - UMR5182 (LC)
École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL)
Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Spectropôle - Aix Marseille Université (AMU SPEC)
Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)
Institut de Chimie Radicalaire (ICR)
Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
CNRS, NSFC (21871216)and Aix-Marseille Université
Université de Lyon, École Normale Supérieure de Lyon, CNRS UMR 5182, Laboratoire de Chimie, 46 allée d'Italie, F69364 Lyon, France
Aix Marseille Univ, CNRS, Centrale Marseille, FSCM, Spectropole, Marseille, France
Source :
Organic Letters, Organic Letters, 2021, ⟨10.1021/acs.orglett.1c00773⟩, Organic Letters, American Chemical Society, 2021, ⟨10.1021/acs.orglett.1c00773⟩
Publication Year :
2021
Publisher :
American Chemical Society (ACS), 2021.

Abstract

International audience; A viologen–phenylene–imidazole (VPI) conjugate, previously shown to be singly complexed by CB[7] and doubly bound by CB[8], is herein shown to form antiparallel triple stacks in water with cucurbit[10]uril (CB[10]), pairwise complexing the guest trimer. The quinary host:guest 2:3 complex showed features assignable to charge-transfer interactions. Under reductive conditions, CB[10] could solubilize a VPI radical, even though CB[10] and reduced VPI are almost insoluble, thereby illustrating a possible new application for CB[10].

Details

ISSN :
15237052 and 15237060
Volume :
23
Database :
OpenAIRE
Journal :
Organic Letters
Accession number :
edsair.doi.dedup.....5f665e95d113dd6bf8fb3e2a6dd41d10
Full Text :
https://doi.org/10.1021/acs.orglett.1c00773