Thiahelicene-based inherently chiral films for enantioselective electroanalysis

Area of Science:

• Electrochemistry
• Chiral Analysis
• Materials Science

Background:

• Chiral electroanalysis represents a high degree of recognition in electrochemical sensing, enabling discrimination between enantiomers.
• Recent advances utilize "inherently chiral" molecular selectors where chirality and function stem from the same structure.
• Existing methods often employ atropisomeric biheteroaromatic scaffolds with axial stereogenicity.

Purpose of the Study:

• To present the enantiodiscrimination capabilities of enantiopure, inherently chiral films derived from a thiahelicene monomer.
• To evaluate the performance of these novel helicoidal stereogenic films against chiral probes of varying nature and size.
• To compare the thiahelicene-based approach with existing inherently chiral selectors featuring axial stereogenicity.

Main Methods:

• Electrooxidation of a thiahelicene monomer to form enantiopure, inherently chiral films.
• Electrochemical evaluation of the enantiodiscrimination performance using different chiral analytes.
• Comparative analysis against atropisomeric selectors with axial stereogenicity.

Main Results:

• Demonstrated enantiodiscrimination capabilities of the novel thiahelicene-based chiral films.
• Achieved high enantiodiscrimination for various chiral probes, indicating broad applicability.
• Confirmed that the high enantiodiscrimination extends to electron spins, similar to atropisomeric selectors.

Conclusions:

• Inherently chiral thiahelicene films offer a promising new platform for advanced chiral electroanalysis.
• This helicoidal stereogenic approach exhibits significant potential, comparable or superior to existing methods.
• The findings expand the scope of inherently chiral selectors for electrochemical enantioseparation and sensing.