Issue 9, 2022

Tweezer-type binding cavity formed by the helical folding of a carbazole–pyridine oligomer

Abstract

We have synthesised a new aromatic foldamer based on the carbazole–pyridine oligomers that adopt helical conformations via dipole–dipole interactions and π-stacking between two ethynyl bond-linked monomers. This foldamer scaffold has been further modified into a synthetic receptor with a tweezer-type binding cavity outside the helical backbone upon folding, in contrast to most aromatic foldamers with internal binding cavities. The tweezer-type cavity is composed of two parallel pyrenyl planes, allowing for the intercalation of a naphthalenediimide guest via π-stacking and CH⋯O interactions, as demonstrated using its 1H NMR spectra and X-ray crystal structure.

Graphical abstract: Tweezer-type binding cavity formed by the helical folding of a carbazole–pyridine oligomer

Supplementary files

Article information

Article type
Communication
Submitted
23 Nov 2021
Accepted
23 Dec 2021
First published
23 Dec 2021

Chem. Commun., 2022,58, 1410-1413

Tweezer-type binding cavity formed by the helical folding of a carbazole–pyridine oligomer

H. J. Jang, S. Lee, B. J. An, G. Song, H. Jeon and K. Jeong, Chem. Commun., 2022, 58, 1410 DOI: 10.1039/D1CC06569F

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