Enantioselective discrimination of alcohols by hydrogen bonding: a SERS study

Abstract

Efficient and generic enantioselective discrimination of various chiral alcohols is achieved by using surface-enhanced Raman scattering (SERS) spectroscopy through charge-transfer (CT) contributions. The relative intensities of the peaks in the SERS spectra of a chiral selector are strongly dependent on the chirality of its surroundings. This highly distinct spectral discrepancy may be due to the tendency of chiral isomers to form intermolecular hydrogen-bonding complexes with the chiral selector in different molecular orientations, resulting in different CT states and SERS intensities of the adsorbates in the system. This study opens a new avenue leading to the development of novel enantiosensing strategies. A particular advantage of this approach is that it is label-free and does not employ any chiral reagents, including chiral light.

Keywords: charge transfer; chiral recognition; hydrogen bonding; surface-enhanced Raman scattering.