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Dynamic multicomponent hemiaminal assembly.

ABSTRACT: A simple approach to generating in situ metal-templated tris-(2-picolyl)amine-like multicomponent assemblies with potential applications in molecular recognition and sensing is reported. The assembly is based on the reversible covalent association between di-(2-picolyl)amine and aldehydes. Zinc ion is best for inducing assembly among the metal salts investigated, whereas 2-picolinaldehyde is the best among the heterocyclic aldehydes studied. Although an equilibrium constant of 6.6×10(3) M(-1) was measured for the assembly formed by 2-picolinaldehdye, di-(2-picolyl)amine, and zinc triflate, the equilibrium constants for other systems are in the 10(2) M(-1) range. X-ray structural analysis revealed that zinc adopts trigonal-bipyramidal geometry within the assembled ligand. The diversity and equilibrium of the assemblies are readily altered by simply changing concentrations, varying components, or adding counteranions.

SUBMITTER: You L

PROVIDER: S-EPMC3506383 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Dynamic multicomponent hemiaminal assembly.

You Lei L Long S Reid SR Lynch Vincent M VM Anslyn Eric V EV

Chemistry (Weinheim an der Bergstrasse, Germany) 20110823 39

A simple approach to generating in situ metal-templated tris-(2-picolyl)amine-like multicomponent assemblies with potential applications in molecular recognition and sensing is reported. The assembly is based on the reversible covalent association between di-(2-picolyl)amine and aldehydes. Zinc ion is best for inducing assembly among the metal salts investigated, whereas 2-picolinaldehyde is the best among the heterocyclic aldehydes studied. Although an equilibrium constant of 6.6×10(3) M(-1) wa ...[more]

PMID: 21919095

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