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Fluorescence visualization of cucurbit[8]uril-triggered dynamic host–guest assemblies

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Abstract

Cucurbit[8]uril (Q[8] or CB[8]), as a synthetic macrocyclic host, plays an important role in constructing various water soluble dynamic supramolecular polymers and materials. Here we report host–guest interactions of Q[8] with π-conjugated bispyridinium guests in aqueous solution that resulted in a series of unprecedented dynamic 2 : 2, 2 : 3, and 1 : 2 assemblies (guest/Q[8]). Most importantly, these subtly different host–guest binding modes could be distinguished by naked-eye observation of the resulting quantitative fluorescence emissions. Further characterization suggested that the Q[8] host-stabilized charge-transfer interactions could be dissociated and controlled by the N-substituted alkyl chains on the cationic guests via the formation of a 2 : 3 quinary complex or a U-shaped conformation, which led to the discovery of new possible binding modes for the Q[8] host.

Graphical abstract: Fluorescence visualization of cucurbit[8]uril-triggered dynamic host–guest assemblies

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Supplementary files

Article information


Submitted
31 May 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Fluorescence visualization of cucurbit[8]uril-triggered dynamic host–guest assemblies

X. Zhang, T. Sun and X. Ni, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00649A

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