Enantioselective sensing of carboxylic acids with a bis(urea)oligo(phenylene)ethynylene foldamer
2019
De los Santos, Zeus A. | Yusin, Georgy | Wolf, Christian
The development of molecular probes for optical sensing of chiral compounds has received increasing attention in recent years, in particular because of the potential to accelerate asymmetric reaction analysis. In this study, we prepared conformationally flexible oligo(phenylene)ethynylene foldamers carrying peripheral bis(trifluoromethyl)phenylurea units that undergo hydrogen bonding with chiral carboxylic acids. This interaction results in a chiral amplification process across the stereodynamic sensor scaffold which coincides with characteristic circular dichroism signals at high wavelengths. The induced chiroptical signals allow quantitative determination of the enantiomeric excess of the substrate which was demonstrated with nonracemic samples of tartaric acid. The chirality sensing assay is fast, sufficiently accurate for high-throughput screening purposes and adaptable to parallel analysis with multiwell plate readers.
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