Modular Introduction of endo-Binding Sites in a Macrocyclic Cavity towards Selective Recognition of Neutral Azacycles.
Angew Chem Int Ed Engl
; 61(26): e202203016, 2022 06 27.
Article
em En
| MEDLINE
| ID: mdl-35417618
ABSTRACT
Macrocycles with a functionalized interior, which is a general cavity feature of bioreceptors, are relatively hard to synthesize. Here we report a modular strategy to customize diverse endo-binding sites in the macrocycle cavity. Only two steps are needed. First, one V-shaped functional module bearing an embedded binding site and two 2,5-dimethoxyphenyls as reaction modules are connected. Then the condensation of the resulting monomer and paraformaldehyde directly produces the designed macrocycle. V-shaped monomers are deliberately used to guarantee the binding sites equatorially directing inward into the cavity and 2,5-dimethoxyphenyls standing axially as macrocycle sidewalls. More than a dozen endo-functionalized macrocyclic receptors have been constructed. Host-guest complexation studies show that macrocycle BP1-decorated interior OH moieties can strongly encapsulate neutral azacycles by forming inner hydrogen bonds, giving a high association constant of 4.59×104 â
M-1 in non-polar media.
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Base de dados:
MEDLINE
Assunto principal:
Compostos Macrocíclicos
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2022
Tipo de documento:
Article