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Chirality Sensing With Stereodynamic Biphenolate Zinc Complexes
Author(s) -
Bentley Keith W.,
Santos Zeus A.,
Weiss Mary J.,
Wolf Christian
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22489
Subject(s) - chemistry , chirality (physics) , circular dichroism , diethylzinc , denticity , enantiomer , zinc , enantiomeric excess , stereochemistry , ligand (biochemistry) , crystallography , catalysis , enantioselective synthesis , organic chemistry , crystal structure , biochemistry , physics , chiral symmetry breaking , receptor , quantum mechanics , nambu–jona lasinio model , quark
Two bidentate ligands consisting of a fluxional polyarylacetylene framework with terminal phenol groups were synthesized. Reaction with diethylzinc gives stereodynamic complexes that undergo distinct asymmetric transformation of the first kind upon binding of chiral amines and amino alcohols. The substrate‐to‐ligand chirality imprinting at the zinc coordination sphere results in characteristic circular dichroism signals that can be used for direct enantiomeric excess ( ee ) analysis. This chemosensing approach bears potential for high‐throughput ee screening with small sample amounts and reduced solvent waste compared to traditional high‐performance liquid chromatography methods. Chirality 27:700–707, 2015 . © 2015 Wiley Periodicals, Inc.