Architecture and function of atropisomeric molecular triads

Area of Science:

• Stereochemistry
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Molecular triads featuring a central aromatic or heteroaromatic unit (B-A-B) can adopt distinct spatial arrangements.
• These arrangements include syn and anti conformers or atropisomers, characterized by C or S shapes.
• Stereoisomers can exist as discrete conformer species or stable atropisomers isolable at ambient temperatures.

Purpose of the Study:

• To explore the conformational and stereoisomeric possibilities of molecular triads.
• To differentiate between conformers and stable atropisomers.
• To investigate the distinct properties and potential applications of syn and anti stereoisomers.

Main Methods:

• Nuclear Magnetic Resonance (NMR) spectroscopy for distinguishing conformer species.
• Separation techniques for isolating stable atropisomers at ambient temperature.
• Evaluation of the properties, such as complex-forming abilities, of separated stereoisomers.

Main Results:

• Identification of syn and anti stereoisomers in molecular triads.
• Demonstration that some stereoisomers exist as stable atropisomers separable at room temperature.
• Observation of differing properties, including complex-forming capabilities, between syn and anti atropisomeric triads.

Conclusions:

• Molecular triads exhibit diverse stereoisomerism, including stable atropisomers.
• Separable atropisomers possess distinct properties valuable for chemical applications.
• Atropisomeric triads show promise as ligands in asymmetric dihydroxylation reactions.