An alpha-chiral primary amine, enantiopure 1,1'-bi-2-naphthol (BINOL), and o-formylphenylboronic acid assemble efficiently and rapidly into chiral host-guest structures, inducing chirality in the system and causing distinct circular dichroism signals for each enantiomer of the amine. Using three different BINOLs to achieve an array of receptors, the CD signals resulting from several amines were processed using several chemometric tools to give satisfactory discrimination of the amines studied. PCA shows that the main contributor to the variance in the system is chirality and LDA was able to identify the different amines with a 100% confidence level, based on identity and chirality. For ee% determination using a calibration curve, the average total error was 5.8%. Competition experiments where BINOL analogues or amines for dynamic fingerprinting of mixtures are underway.

Multi-component assembly studies for chemo and enantiodiscrimination of alpha-chiral primary amines

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.