Issue 7, 2021

Template-driven construction of [8]-imidazolium macrocycles

Abstract

Tetrakisimidazolium macrocycles have been widely used in supramolecular chemistry due to their inherently cationic nature and sizable cavity. However, [n]-imidazolium macrocycles (n > 4) are rather undeveloped. Reported here is a controllable synthetic strategy for [n]-imidazolium (n = 8) macrocycles, which involves the formation of metal–carbene templates, a double [2 + 2] photocycloaddition and the subsequent removal of metal ions. Two octakisimidazolium macrocycles H8-2a(PF6)8 and H8-2b(PF6)8 were prepared from linear tetrakisimidazolium salts H4-1a(PF6)4 and H4-1b(PF6)4. More significantly, the present work not only further verified the strategy of metal–carbene templated photochemical [2 + 2] cycloaddition for the construction of novel polyimidazolium macrocycles, but also offers a new synthetic approach for the preparation of functional acceptors for molecule recognition.

Graphical abstract: Template-driven construction of [8]-imidazolium macrocycles

Supplementary files

Article information

Article type
Research Article
Submitted
23 dec 2020
Accepted
03 jan 2021
First published
04 jan 2021

Org. Chem. Front., 2021,8, 1431-1436

Template-driven construction of [8]-imidazolium macrocycles

K. Hua, M. Gan, X. Liu, L. Zhang, Y. An and Y. Han, Org. Chem. Front., 2021, 8, 1431 DOI: 10.1039/D0QO01617A

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