Issue 16, 2021

Aqueous assembly of a (pseudo)rotaxane with a donor–π–acceptor axis formed by a Knoevenagel condensation

Abstract

The incorporation of a linear D–π–A “push–pull” chromophore synthesized by a Knoevenagel condensation as axle of a rotaxane is reported. While the introduction of the mechanical stoppers by the reversible and thermodynamically controlled Knoevenagel reaction turned out to be challenging, mechanical fixation of the superstructure is achieved by “click” chemistry in aqueous solution. The isolated rotaxane with a red- to NIR-emitting dye as axle displays enhanced emission in aqueous buffered media compared to the unthreaded model chromophore.

Graphical abstract: Aqueous assembly of a (pseudo)rotaxane with a donor–π–acceptor axis formed by a Knoevenagel condensation

Supplementary files

Article information

Article type
Research Article
Submitted
27 apr 2021
Accepted
12 iyn 2021
First published
14 iyn 2021
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2021,8, 4399-4407

Aqueous assembly of a (pseudo)rotaxane with a donor–π–acceptor axis formed by a Knoevenagel condensation

L. Jucker, Y. Aeschi and M. Mayor, Org. Chem. Front., 2021, 8, 4399 DOI: 10.1039/D1QO00643F

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