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School of Physical and Chemical Sciences

Enantioselective Synthesis of Heterohelicenes through π-extension

Research Group: Chemistry
Number of Students: 1
Length of Study in Years: 4 Years
Full-time Project: yes

Funding

This studentship is funded via a studentship from the China Scholarship Council.  CSC is offering a monthly stipend to cover living expenses and QMUL is waving fees and hosting the student. These scholarships are available only for Chinese candidates. 

Project Description

Helicenes are helically chiral aromatic molecules that have been intensively studied for their potential to transform modern consumer devices. Their intense chiroptical properties have allowed the fabrication of circularly polarised OLEDs, which could be twice as bright as conventional screens when used in combination with a common anti-glare filter. Additionally, helicenes have shown spin filtering through the Chiral Induced Spin Selectivity (CISS) effect, which could lead to much faster and more efficient devices that exploit organic spintronics. Helicenes are particularly promising candidates for commercialisation as they possess much higher charge transport and processability compared to the most commonly investigated CISS substrates (DNA or oligopeptides). Despite these attractive properties, helicenes are not yet fulfilling their potential due to synthetic challenges. While concise and elegant helicene syntheses exist, these are limited to specific substrates and substitution patterns. Helicenes that do not follow these patterns usually have to be prepared using a stepwise process that is cumbersome and requires photochemical reactions that can be difficult to scale beyond tens of milligrams.

 

Current research in my group is addressing this scalability by developing a photochemical synthesis of helicenes in continuous flow that has shown robust yields from scales of 100 mg (74% yield) to 1.1 g (70% yield). Yet this approach (like most helicene syntheses) only produces racemic material, which must be laboriously resolved into the two enantiomers.

 

The proposed project aims to address this synthetic problem by developing an enantioselective transition-metal catalysed π-extension to assemble two small and easily accessible fragments into enantiomerically enriched helicenes. The methodology would greatly improve access to bespoke helicene structures by reducing the number of synthetic steps and eliminating the need for costly chiral resolution.

 

 

Requirements

Applications are invited from outstanding candidates with or expecting to receive a first or upper-second class master's degree in Chemistry or an area relevant to the project. A standalone master's degree, or undergraduate integrated master's degree are required for this position.

The ideal candidate should have some experience in synthetic chemistry and be interested in exploring a highly interdisciplinary, collaborative, and dynamic field of scientific research. 

Applicants are encouraged to contact Dr Jochen Brandt on j.brandt@qmul.ac.uk prior to their submission by sending a CV and a description of their interests and expertise relevant to the project.

Please use the link below to apply for this project:

https://www.qmul.ac.uk/spcs/phdresearch/application-process/#apply

Deadline for applications - 31st of January 2023

 

SPCS Academics: Dr Jochen Brandt