Paradigms of Stereoselectivity and Molecular Dynamics: Using Light to Transfer Molecular Chirality and to Control Molecular Rotation

Utilizing light, a massless reagent and stimulus, to transform molecular scaffolds and to control molecular interactions is an elegant approach to minimize chemical wastes. In recent years, various research groups have adopted photochemical transformations as key steps and environmentally benign protocols in the synthesis of a number of molecular building blocks that display unique stereochemical properties. Nevertheless, controlling and transferring stereochemical information during light-driven processes continues to be a challenging task for chemists.

To achieve higher stereoselectivities during photochemical reactions, Ayitou has designed various axially chiral substrates that could remember their chiral information upon photo-excitation leading to chirally-enriched photoproducts. In addition, he has been investigating the rotational dynamics of photoresponsive crystalline molecular rotors upon light-induced structural changes of the photoresponsive group.

In the first part of this presentation, Ayitou will highlight the stereospecific 6p-photocyclization of axially chiral acrylanilides to afford chirally-enriched 3,4-dihydro-quinolinones photoproducts. The second part of the presentation will detail the synthesis, crystallography profiles, photophysical behaviors and rotational dynamics of photoresponsive crystalline molecular rotors.