Enantioselective molecular recognition in a flexible self-folding cavitand

09 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The dynamic features of the host have been studied by 1H NMR spectroscopy, revealing a bowl inversion motion that is slow in the NMR time scale. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diasteromeric host-guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced fit behavior with regards to resorcin[4]arene derived self-folding cavitands.

Keywords

Host-guest systems
Cavitands
Enantioselective molecular recognition
Induced fit
Chiral ammonium salts

Supplementary materials

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Description
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Supporting Information
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Experimental procedures, characterization data, details for titration experiments, details for the MD simulations
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Supporting video 1
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Video of the MD trajectory for 1
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Supporting video 2
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Video of the MD trajectory for S-3
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Supporting video 3
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Video of the MD trajectory for S-3 with bound (R)-G3
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Supporting video 4
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Video of the MD trajectory for S-3 with bound (S)-G10
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