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  Stereoselective synthesis of mechanically chiral molecules for sensing and catalysis


   School of Chemistry

   Applications accepted all year round  Funded PhD Project (UK Students Only)

About the Project

Background – the stereoselective synthesis of mechanically chiral molecules

The stereoselective synthesis of chiral organic molecules is one of the core challenges in synthetic organic chemistry. Mechanically interlocked molecules such as rotaxanes and catenanes can be chiral even when their individual components are not, a feature of their structures that is attracting increasing attention. Although such molecules are often considered to be the preserve of supramolecular chemistry, modern methods such as the active template approach bring their synthesis to the interface with synthetic organic chemistry.

The Goldup Group (https://golduplab.org/) at the University of Birmingham have pioneered the active template synthesis of such “mechanically chiral molecules” to deliver the first stereoselective methods to access the enantiomers of mechanically chiral rotaxanes and catenanes (Nat. Chem. 2022: https://doi.org/10.1038/s41557-021-00825-9; Nat. Chem. 2022: https://doi.org/10.1038/s41557-022-00973-6; Chem 2023 https://doi.org/10.1016/j.chempr.2023.01.009; Nat. Chem. 2023 https://doi.org/10.1038/s41557-023-01194-1). Alongside this work, they have revolutionised the theory of mechanical stereochemistry (Chem. Soc. Rev. 2018 https://doi.org/10.1039/C8CS00097B), which has led to the discovery of new classes of mechanically chiral molecules and the development of clearly articulated methodological approaches for their synthesis (Chem 2020 https://doi.org/10.1016/j.chempr.2020.07.012).

The project – mechanically chiral molecules as catalysts

A key advantage of mechanically chiral molecules is that threading one molecule through another creates an unusual, crowded environment, a feature that is increasingly being exploited in catalysis (Nat. Rev. Chem. 2022 https://doi.org/10.1038/s41570-021-00348-4). The successful candidate will study the applications of mechanically chiral molecules as enantioselective catalysts; preliminary investigations suggest such molecules have significant promise in this area (Chem 2020 https://doi.org/10.1016/j.chempr.2020.02.006). To do this, they will apply the Goldup Group’s existing methodologies for the synthesis of chiral catenane and rotaxane-based ligands and organocatalysts, as well as developing new synthetic methodologies as required. The ideal candidate will be excited by the challenge of synthesising molecules stereoselectively and the development of new catalytic processes.

Relevant reviews

The chemistry of interlocked molecules: Chem. Commun. 2014, https://doi.org/10.1039/C3CC47842D

Mechanically interlocked ligands: Chem. Commun. 2017, https://doi.org/10.1039/C6CC07377H

Chiral interlocked molecules: Chem. Soc. Rev. 2018, https://doi.org/10.1039/C8CS00097B

Rotaxanes and catenanes in catalysis: Nat. Rev. Chem. 2022: https://doi.org/10.1038/s41570-021-00348-4

Training and mentoring

The successful candidate will receive training in synthetic organic and supramolecular chemistry and other specialist areas as required by their project, either from the Goldup Group or appropriate collaborators. They will gain extensive experience of a range of analytical techniques including advanced NMR analysis, single crystal x-ray diffraction and HPLC analysis. They will be mentored by Professor Goldup to improve their scientific writing, presentation skills and ability to design and execute new scientific projects. Completing a PhD in the Goldup Group will prepare students for leadership roles in scientific research, as well as positions across the scientific sector more generally.

The Goldup Group

Research in the Goldup Group (https://golduplab.org/) at the University of Birmingham focusses on the synthesis, properties and applications of mechanically interlocked molecules such as rotaxanes and catenanes. This work takes place at the interface of organic synthetic and supramolecular chemistry and requires collaborations with a range of other disciplines from materials science to chemical biology.

Funding

This studentship is fully funded for 3.5 years and includes a tax-free annual stipend (currently £18,622) and fees (currently £4,712) at the UK home rate. Please note that, due to funding restrictions, applicants not eligible for UK home fee status will only be considered in exceptional circumstances.

Application process

Interested candidates should contact Professor Goldup by email () in the first instance with a copy of their CV and a covering letter outlining their research interests. The School of Chemistry is keen to achieve a gender and diversity balance across the School and welcome applicants from all backgrounds. The School holds an Athena SWAN Bronze Award, which recognises its work in promoting women’s careers in science, technology, engineering, mathematics and medicine (STEM) in higher education.

Chemistry (6)

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