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Enantioselective Discrimination of Alcohols by Hydrogen Bonding: A SERS Study
Author(s) -
Wang Yue,
Yu Zhi,
Ji Wei,
Tanaka Yoshito,
Sui Huimin,
Zhao Bing,
Ozaki Yukihiro
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201407642
Subject(s) - enantioselective synthesis , chirality (physics) , hydrogen bond , intermolecular force , raman spectroscopy , reagent , raman scattering , chemistry , chemical physics , materials science , chiral symmetry , computational chemistry , photochemistry , molecule , organic chemistry , catalysis , optics , physics , quantum mechanics , nambu–jona lasinio model , quark
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.