A supramolecular sorting hat: stereocontrol in metal-ligand self-assembly by complementary hydrogen bonding

Michael C Young; Lauren R Holloway; Amber M Johnson; Richard J Hooley

doi:10.1002/anie.201405242

A supramolecular sorting hat: stereocontrol in metal-ligand self-assembly by complementary hydrogen bonding

Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9832-6. doi: 10.1002/anie.201405242. Epub 2014 Jul 17.

Authors

Michael C Young¹, Lauren R Holloway, Amber M Johnson, Richard J Hooley

Affiliation

¹ University of California Riverside, Department of Chemistry, Riverside, CA 92521 (USA).

PMID: 25044629
DOI: 10.1002/anie.201405242

Abstract

A combination of self-complementary hydrogen bonding and metal-ligand interactions allows stereocontrol in the self-assembly of prochiral ligand scaffolds. A unique, non-tetrahedral M4L6 structure is observed upon multicomponent self-assembly of 2,7-diaminofluorenol with 2-formylpyridine and Fe(ClO4)2. The stereochemical outcome of the assembly is controlled by self-complementary hydrogen bonding between both individual ligands and a suitably sized counterion as template. This hydrogen-bonding-mediated stereoselective metal-ligand assembly allows the controlled formation of nonsymmetric discrete cage structures from previously unexploited ligand scaffolds.

Keywords: diastereoselectivity; hydrogen bonding; ligand effects; self-assembly; supramolecular chemistry.