Translation of novel multicomponent reactions to practical [8]annulene-based functional molecules and material

[8]Annulenes are eight-member ring hydrocarbons with alternating single and double bonds.

As a result of ring-strain, they adopt a specific concave geometry that combined with not fulfilling Hückels rule reflect in a number of unique properties such as a fluxional topology, resistance to cyclometallation, and shape-shifting response to redox changes. Each, an attractive design feature for ligands and responsive materials.

Exploitation of these properties is however held back by synthetic shortcomings.

The purpose of this proposal is to bridge this gap by developing  multicomponent approaches to [8]annulene derivatives that maps onto applications in asymmetric catalysis and new responsive materials.Broadly, as the consumption of synthetic materials increases over time, so does the need for reducing the footprint of chemcial syntheses.

Moreover, benign molecules that avoids potentially harmful functional groups or elements is a pursuit of emerging importance.

In addition to the synthetic advances, this proposal embraces both these aspects by developing new classes of chiral catalysts that seeks to exploit the cyclometallation-resistance of [8]annulene ligands, and new types of shape-shifting pure hydrocarbon materials.

A third purpose is to clarify design principles underlying the relationship between molecular structure and function in [8]annulenes with a longer term vision is to inspire and enable further uses of this intriguing core.