Tuesday, August 23, 2011

Dynamic Multicomponent Hemiaminal Assembly

Dynamic Multicomponent Hemiaminal Assembly:

Eur J Chem

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 6.6×103M−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 102M−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.

Thumbnail image of graphical abstract

Change the diversity! A simple metal-mediated multicomponent assembly based on reversible covalent bond formation is described (see scheme). The diversity of the system can be easily varied with the potential for dynamic combinatorial library creation and subsequent molecular recognition.

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