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Mechanical Chirality: Synthesis, Properties and Applications at a New Horizon in Supramolecular Stereochemistry

Periodic Reporting for period 3 - MechaniChiral (Mechanical Chirality: Synthesis, Properties and Applications at a New Horizon in Supramolecular Stereochemistry)

Reporting period: 2020-04-01 to 2021-09-30

Molecular chirality, the ability for molecules to exist in two mirror image forms in the same way that left and right hands do, is a central theme in chemistry; each year >10% of publications in leading chemistry journals concerned chirality. Chirality can arise due to several different struvtural features and all of those studied so far have found applications throughout the sub-disciplines of chemistry including as catalysts, materials and sensors.

Mechanically chiral rotaxanes are molecules in which the threading of a linear dumbbell shaped component through a ring shaped component leads to the appearance of chirality, as opposed to the structure of the ring or dumbbell components themselves. These unusual molecules represent a novel and unexplored class of chiral molecules. However, the lack of a scalable methods for their isolation has prevented all but the most cursory investigation of their properties. Thus, mechanical chirality remains an unexplored frontier in chemistry with the potential to deliver novel functions and impact across a range of chemical disciplines from materials chemistry to the synthesis of pharmaceutically active compounds.

Within the period of this ERC Consolidator Grant Prof Stephen Goldup will lead a team to investigate the synthesis, properties and applications of these intriguing mechanically chiral molecules.
During the first half of the project we have achieved the following key breakthroughs:

1) New, general scalable methods to make mechanically chiral rotaxanes

We have developed new chemical techniques that allow us to make new types of mechanically chiral molecules. These methods have opened up the structures whose properties and applications can be investigated

2) Mechanically chiral sensors

We have developed mechanically chiral rotaxanes that interact with other small molecules to provide information about the purity of samples and their properties. Having demonstrated this principle we are now developing practical examples that can be used in the development of new chemical reactions and the analysis of medically relevant samples.

3) Mechanically chiral catalysts

We have demonstrated the first examples of catalysts based on mechanically chiral molecules. With prototypes in hand, we are now investigating the benefits of this new approach to catalyst development.
Despite the relatively early stage of the project we have already achieved many of the key objectives set out in the proposal. The second half of the project will focus on taking our prototype systems towards molecules with real-world applications, as well as improving our chemical techniques and understanding of these unusual molecules.
Image of chiral rotaxanes and catenanes