Post-Synthesis Conversion of an Unstable Imine Cage to a Stable Cage with Amide Moieties Towards Selective Receptor for Fluoride

Bhandari, P and Mukherjee, PS (2022) Post-Synthesis Conversion of an Unstable Imine Cage to a Stable Cage with Amide Moieties Towards Selective Receptor for Fluoride. In: Chemistry - A European Journal .

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Abstract

Synthesis of robust covalent macrocycles/cages via multiple amide-bond forming reaction is highly challenging and generally it needs multistep reactions. One-pot reaction of appropriate di-/tri-acyl chloride with a diamine generally results polymers or oligomers instead of discrete architectures. To overcome this limitation, a strategy is reported here using dynamic imine chemistry for facile construction of imine-based macrocycle and cage upon treatment of a diamine with di- and tri-aldehydes respectively, followed by post-synthesis one-step conversion of imine bonds to amides to form the desired robust macrocycle and cage containing multiple amide bonds. While the macrocycle was found to form aggregates in DMSO, the cage was intact without any aggregation. Six amide groups in the confined pocket of the cage made it an ideal receptor for selective binding of fluoride with very high selectivity (∼3 (Formula presented.) 103 fold) over chloride, and it was silent towards other halides, phosphate, and other oxyanions.

Item Type:	Journal Article
Publication:	Chemistry - A European Journal
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc.
Keywords:	cage compounds; host-guest; post-synthesis; self-assembly; supramolecular chemistry
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	24 Sep 2022 06:55
Last Modified:	24 Sep 2022 06:55
URI:	https://eprints.iisc.ac.in/id/eprint/76665

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