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

Fengbo Liu, Shagor Chowdhury, Roselyne Rosas, Valérie Monnier, Laurence Charles, Hakim Karoui, Didier Gigmès, Olivier Ouari, Floris Chevallier, Christophe Bucher, Anthony Kermagoret, Simin Liu, David Bardelang

2021Organic Letters23 citationsDOIOpen Access PDF

Abstract

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].

Topics & Concepts

ChemistryViologenStack (abstract data type)Derivative (finance)Combinatorial chemistryTriple bondStereochemistryPhotochemistryOrganic chemistryComputer scienceOperating systemBusinessDouble bondFinanceSupramolecular Chemistry and ComplexesCrystallography and molecular interactionsAdvanced NMR Techniques and Applications