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Expanding structural diversity in a library of disulfide macrocycles through in-situ imide hydrolysis.

ABSTRACT: We describe here an unorthodox approach to dynamic covalent chemistry in which the initially-unexpected in-situ hydrolysis of a bis-imide is employed to control the composition of a library of structurally diverse macrocycles. A single building block is used to generate a library of numerous disulfide-based architectures in a one-pot single-step process. The dual-stimuli method is based on simultaneous changes in pH and DMSO concentration to expand the structural diversity of the macrocyclic products. Mechanistic details of this complex process are investigated by the kinetics analysis. We delivered a facile strategy for the synthesis of water-soluble, multicomponent and dynamic macrocycles equipped with number of different functional groups, thus giving a prospect of their application in guest-driven phase transfer.

SUBMITTER: Konopka M

PROVIDER: S-EPMC8742088 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Expanding structural diversity in a library of disulfide macrocycles through in-situ imide hydrolysis.

Konopka Marcin M Stefankiewicz Artur R AR

Scientific reports 20220107 1

We describe here an unorthodox approach to dynamic covalent chemistry in which the initially-unexpected in-situ hydrolysis of a bis-imide is employed to control the composition of a library of structurally diverse macrocycles. A single building block is used to generate a library of numerous disulfide-based architectures in a one-pot single-step process. The dual-stimuli method is based on simultaneous changes in pH and DMSO concentration to expand the structural diversity of the macrocyclic pro ...[more]

PMID: 34997018

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