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Dynamic Multicomponent Hemiaminal Assembly
Author(s) -
You Lei,
Long S. Reid,
Lynch Vincent M.,
Anslyn Eric V.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201101085
Subject(s) - chemistry , trifluoromethanesulfonate , zinc , amine gas treating , trigonal bipyramidal molecular geometry , equilibrium constant , ligand (biochemistry) , hemiaminal , metal , covalent bond , combinatorial chemistry , molecule , polymer chemistry , inorganic chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
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.