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

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-typ...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-01, Vol.58 (9), p.141-1413
Main Authors: Jang, Hye Jin, Lee, Seungwon, An, Byung Jun, Song, Geunmoo, Jeon, Hae-Geun, Jeong, Kyu-Sung
Format: Article
Language:English
Subjects:
Binding
Carbazoles
Crystal structure
Dipole interactions
Folding
Holes
NMR
Nuclear magnetic resonance
Oligomers
Pyridines
Stacking
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Summary: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 1 H NMR spectra and X-ray crystal structure. Helical folding of a carbazole-pyridine oligomer generates a tweezer-type binding cavity which allows for the intercalation of a naphthalenediimide guest.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06569f