Chemical sensors are powerful for the fast recognition of chiral compounds. However, the established sensing systems are less effective for chiral tertiary alcohols. The chiral tertiary alcohol group is an important structural unit in natural products and drug molecules, and its enantioselective recognition represents a significant and challenging task. In this paper, a novel type of chiral bisselenourea sensor was first synthesized and used as a strong hydrogen-bonding donor for highly efficient chiral recognition of a diverse range of tertiary alcohols. The obtained sharply split NMR signals are well-distinguishable with a large (up to 0.415 ppm) chemical shift nonequivalence. The NMR signal of the hydroxyl hydrogen atom was first employed for enantiomeric excess determination of tertiary alcohols, giving accurate results with <2% absolute errors. The 2D NOESY spectra and computational studies suggest that the geometrical differentiation of the formed diastereomeric complexes between the sensor and tertiary alcohols enables the chiral discrimination of the hydroxyl hydrogen signals of the tertiary alcohol in the ¹H NMR spectrum.

A novel chiral octahedral rhodium complex containing fluorine has been developed to be an excellent chiral sensor for a variety of amines including diamines, monoamines, amino alcohols and amino acids, showing well distinguishable ¹⁹ F NMR signals and an accurate measurement of enantiomeric determination.

Atropisomerism is one of the basic concepts in stereochemistry. Chiral crystals of stereochemically labile atropisomers that originated from Mirror Symmetry Breaking (MSB) can only be characterized by solid-state chiroptical techniques. Herein, solid-state circular dichroism and UV-Vis spectra of six atropisomeric compounds (most of them were obtained from MSB) have been studied. A concentration effect including a wavelength shift and inverse concentration-dependence has been found and preliminarily explained by the absorption flattening effect, scattering effect and the torsion in the molecular structures.