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Organic chemistry, structural electronics and assembly of 3D redox-active helicenes


   Department of Chemistry

   Applications accepted all year round  Self-Funded PhD Students Only

About the Project

Background

Do you have a knack for organic synthesis? Are you driven by wanting to understand how molecular structure and 3D shape can influence π-electronic properties, aromaticity and supramolecular assembly -- sometimes in unusual and unexpected ways? Are you excited by the thought of designing functional organic molecules with a potential to advance energy-related technologies? Collaborating with experts in interdisciplinary fields? That’s great, so are we!

Our research team is seeking an enthusiastic and talented PhD candidate in the area of organic chemistry and supramolecular assembly of functional molecular materials. Using chemistries being developed by the Avestro Group at York, the PhD student will pursue the synthesis of redox-active helicenes that possess non-planar / curved π-conjugated surfaces with right-handed or left-handed helical chirality. The electroactive framework of the target helicenes resemble the well-established class of aromatic diimides (e.g., naphthalene and perylene diimides), which have already been widely explored in the context of aromatic self-assembly for long-range electron delocalisation within organic semiconductors and electroactive polymers, chemical sensing, for energy storage, as photoactive dyes for solar cells, photocatalysis and even as markers for biodiagnostics. Therefore, the student can expect to investigate the fundamental structural and electronic properties of new helicene molecules as they may apply to these long-term applications (i.e., pursued in collaboration with other research groups). Moreover, isolation of helically chiral enantiomers of redox-active helicenes would enable new studies of circularly polarised luminescience and chiral-induced electrochemical behaviour (i.e., in electronic devices).

Objectives

The Student will embark on exploratory, hypothesis-driven research to design and synthesise redox-active helicenes inspired by well-established aromatic diimides. As a member of the Molecular Materials Research Grouping at York, the student will receive interdisciplinary training in multi-step organic synthesis, X-ray crystallography, supramolecular assembly and cutting-edge spectroscopic, electrochemical and electron microscopy techniques to fully investigate the consequences of molecular structure on fundamental and material properties. They will also make use of density functional theory calculations to understand experimental results and predict electronic properties, i.e., in order to rationally design and tailor new organic materials.

- In Years 1 and 2, the Student will pursue the development of redox-active helicenes with π-extended polyaromatic frameworks that encourage greater electronic stabilisation and also configurational stability in order to isolate chiral enantiomers by chiral HPLC. Extended structures may include heteroatoms or other side groups to introduce new and desirable functional properties to their molecules. Helical structures may be synthetically π-extended to form non-planar super macrocycles for study as novel hosts and aromatic systems. Synthetic work may involve air-free Schlenk techniques and/or the use of an air-free glove box.

- They will use a combination of 1D/2D NMR spectroscopies, absorption and emission spectroscopies, electrochemistry, and spectroelectrochemistry to fully elucidate the electronic properties of their molecules and their other redox states. Because molecules will be electron acceptors, we are interested in studying their properties of their reduced forms (e.g., as organic radicals, etc.)

- They will work alongside X-ray crystallographers to understand the supramolecular interactions of their molecules in the solid state, which may help to inform self-assembly behaviour observed in solutions and/or gels.

- They will also pick up skills in DFT computational analysis to model and predict structural and electronic features that may support their experimental observations. We are particularly interested in understanding how the 3D non-planar structure influences energy levels, electronic distributions and aromaticity within the π-conjugated framework.

- Towards Year 3, as materials with desirable properties are realised, the Student will have opportunities in to pursue organic electronic and energy storage device studies, gaining experience either within the Avestro Group (organic batteries, thin-film transistors) or by engaging with our collaborators based at Durham University, Northumbria University and/or Imperial College London (conductive liquid crystals, organic light-emitting diodes, chiroptical transistors).

Research Culture

The Avestro Group is international and culturally diverse, representing different backgrounds, experiences and personalities that help to nurture excellent science in a social and inclusive environment. Our team strives to promote open communication and a “grow together” policy. Individual wellbeing and work–life balance matters. Quality always trumps quantity. Transparency builds trust. “Stupid questions” are great questions. Small successes are still celebrated where “your success is everyone’s success.” All researchers exercise an equal active role in steering the direction of group research. Collaboration between group members is strongly encouraged, and we hope the Student will take advantage when opportunities present themselves.

All Chemistry research students have access to our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills: https://www.york.ac.uk/chemistry/postgraduate/cdts/ 

The Department of Chemistry holds an Athena SWAN Gold Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel: https://www.york.ac.uk/chemistry/ed/ .


Funding Notes

This project is open to students who can fund their own studies or who have been awarded a scholarship separate from this project. The Chemistry Department at York is pleased to offer Wild Fund Scholarships to new students who will pay tuition fees at the overseas rate. Scholarships are competitive and awarded based on academic ability and financial need. For further information see: View Website

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