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Ultramacrocyclization in water via external templation.

ABSTRACT: Condensing a dihydrazide and each of a series of cationic bisaldehyde compounds bearing polymethylene chains in weakly acidic water produces either a macrocycle in a [1 + 1] manner or its dimer namely a [2]catenane, or their mixture. The product distribution is determined by the length of the bisaldehydes. Addition of cucurbit[8]uril (CB[8]) drives the catenane/macrocycle equilibria to the side of macrocycles, by forming ring-in-ring complexes with the latter. When the polymethylene unit of the bisaldehyde is replaced with a more rigid p-xylene linker, its self-assembly with the dihydrazide leads to quantitative formation of a [2]catenane. Upon addition of CB[8], the [2]catenane is transformed into an ultra-large macrocycle condensed in a [2 + 2] manner, which is encircled by two CB[8] rings. The framework of this macrocycle contains one hundred and two atoms, whose synthesis would be a formidable task without the external template CB[8]. Removal of CB[8] with a competitive guest leads to recovery of the [2]catenane.

SUBMITTER: Chen Q

PROVIDER: S-EPMC8768864 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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Ultramacrocyclization in water <i>via</i> external templation.

Chen Qiong Q Lei Ye Y Wu Guangcheng G Li Qing Q Pan Yuanjiang Y Li Hao H

Chemical science 20220105 3

Condensing a dihydrazide and each of a series of cationic bisaldehyde compounds bearing polymethylene chains in weakly acidic water produces either a macrocycle in a [1 + 1] manner or its dimer namely a [2]catenane, or their mixture. The product distribution is determined by the length of the bisaldehydes. Addition of cucurbit[8]uril (CB[8]) drives the catenane/macrocycle equilibria to the side of macrocycles, by forming ring-in-ring complexes with the latter. When the polymethylene unit of the ...[more]

PMID: 35173945

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Ultramacrocyclization in water via external templation.

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Ultramacrocyclization in water <i>via</i> external templation.

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