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

Fengbo Liu (1) , Shagor Chowdhury (2) , Roselyne Rosas (3) , Valérie Monnier (3) , Laurence Charles (4) , Hakim Karoui (4) , Didier Gigmes (4) , Olivier Ouari (4) , Floris Chevallier (2) , Christophe Bucher (2) , Anthony Kermagoret (4) , Simin Liu (1) , David Bardelang (4)

1 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
2 LC - Laboratoire de Chimie - UMR5182
3 AMU SPEC - Spectropôle - Aix Marseille Université
4 ICR - Institut de Chimie Radicalaire

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].

Domains: Chemical Sciences

Fengbo Liu, Shagor Chowdhury, Roselyne Rosas, Valérie Monnier, Laurence Charles, et al.. Triple Stack of a Viologen Derivative in a CB[10] Pair. Organic Letters, 2021, ⟨10.1021/acs.orglett.1c00773⟩. ⟨hal-03227458⟩