Issue 52, 2022

Neutral isocyanide-templated assembly of pillar[5]arene [2] and [3]pseudorotaxanes

Abstract

Unprecedented pillar[5]arene–isocyanide pseudorotaxane complexes are reported. Extensive 1H-NMR experiments reveal remarkably strong binding affinities of alkyl diisocyanide guests (Ka > 105 M−1 in CDCl3) by pillar[5]arenes. Characterised by multinuclear 1H and 13C-NMR spectroscopy and single-crystal X-ray diffraction, it is demonstrated that pillar[5]arenes are capable of encapsulating a series of alkyl diisocyanides wherein either [2]- or [3]pseudorotaxanes can be formed by varying the alkyl chain length. Moreover, electron-deficient aryl isocyanides, are demonstrated to form inclusion complexes within the cavities of pillar[5]arenes stabilised by multiple C–H⋯π interactions.

Graphical abstract: Neutral isocyanide-templated assembly of pillar[5]arene [2] and [3]pseudorotaxanes

Supplementary files

Article information

Article type
Communication
Submitted
20 4 2022
Accepted
31 5 2022
First published
01 6 2022

Chem. Commun., 2022,58, 7253-7256

Neutral isocyanide-templated assembly of pillar[5]arene [2] and [3]pseudorotaxanes

K. Khamphaijun, P. Namnouad, A. Docker, A. Ruengsuk, J. Tantirungrotechai, R. Díaz-Torres, D. J. Harding and T. Bunchuay, Chem. Commun., 2022, 58, 7253 DOI: 10.1039/D2CC02255A

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