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R.J.Whitby@soton.ac.uk

Professor Richard J Whitby 

Professor of Organic Chemistry

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Professor Richard J Whitby is Professor of Organic Chemistry within Chemistry at the University of Southampton.

Richard Whitby graduated with a BA in Natural Sciences from Trinity College, Cambridge University in 1982. After a PhD with Professor P. G. Sammes at the University of Leeds and a fellowship with Professor P. J. Kocienski at the University of Southampton he was appointed to a lectureship at Southampton in 1988. In 1995 he was awarded the Society of the Chemical Industry 'Young Chemists' award, the Zeneca Research Award in Organic Chemistry and the Pfizer Research Award in Chemistry. In 1996, Richard Whitby became a Reader and was also awarded the GlaxoWelcome 'Innovative Chemistry' Research Award. He was promoted to Professor of Organic Chemistry in 1999, the year in which he received the Royal Society of Chemistry Bader award.

He has published chapters in two books on zirconium chemistry, contributed to special issues of Tetrahedron and Synthesis dedicated to Organotransition metal chemistry applied to organic synthesis and presented his work at many international conferences.

He originated and leads the ‘Dial-a-Molecule’ Grand Challenge which has the 20-40 year aim of making the synthesis of new molecules as quick and easy as it currently is to order a commercial compound.

His research interests include total synthesis, particularly using transition metal chemistry to rapidly assemble structures; The synthesis and properties of endohedral fullerenes (such as CH4@C60) made using a process termed molecular surgery; The development of flow and automated chemistry, particularly using in-situ analysis to allow rapid optimization and mechanistic investigation; Synthesis of novel polyaromatic and heteroaromatic compounds for applications in organic electronics, photovoltaics, and Organic Light Emitting Diodes.

B.A., Natural Science, Cambridge, 1982

PhD, Chemistry. University of Leeds, 1985 

Research interests

Prof. Whitby’s research interests span a wide range from using synthetic chemistry to tackle important scientific and societal problems, to developing the technology and informatics of synthesis itself. Current research interests include:

Endohedral Fullerenes. Fullerenes such as C60 containing an endohedral species A, denoted A@C60, are of great theoretical interest, and may have useful applications. We synthesise these molecules by using chemical reactions to open a hole in the fullerene, insert the endohedral species, then use a further series of reaction to re-close (suture) the cage, the overall process being described as molecular surgery. We have developed improved routes to H2@C60, H2O@C60 and He@C60, and made HF@C60, CH4@C60, Ne@C60 and Ar@C60 for the first time. The molecules have fascinating quantum properties due to quantised translation, as well the interaction between nuclear spins and rotational states which are investigated by many national and international groups.

Flow chemistry. We are developing new synthetic methods which take advantage of flow chemistry (continuous processing) techniques. A particular interest is to use flow techniques, particularly with the use of in-line IR, UV, and HPLC-MS, to allow rapid kinetic characterisation and optimisation of reactions.

Organic optoelectronics. We are designing and synthesising molecules with useful optoelectronic properties for application in Organic Light Emitting Diodes, particularly for use in printable devices. The work is lead by high level ab-inito calculations on properties. The current focus is on polyaromatic and heteroaromatic systems.

Past projects involved:

New synthetic methods using transition metals and application to organic synthesis. Our work focuses on various tandem processes using zirconocene templates to rapidly assemble complex organic structures. Particularly powerful has been methods based on the insertion of carbenoids into organozirconocene chlorides or zirconacycles. We have applied zirconium mediated key steps to the synthesis of several natural products. We have also developed a novel approach to chiral zirconocene complexes and applied them to catalytic carbomagnesiation and carboalumination reactions.

Ligands for Orphan Nuclear Receptors. We developed the first small molecule agonists for the important nuclear receptors SF-1 and LRH-1 with potential for application in a variety of biological and therapeutic areas including Stem Cell research and several cancers. Our molecules have been used in 20 laboratories worldwide to investigate the biology of these receptors.

“Dial-a-Molecule” is an EPSRC funded Grand Challenge network which I lead. It is aimed at making the synthesis of novel molecules as quick as it currently is to order a stock chemical. A key to Dial-a-Molecule is to be able to predict the outcome of novel reactions, and hence the best way to do them and the best synthetic route.

Research Projects

Synthesis of Endohedral Fullerenes

Use of Flow Chemistry for the rapid acquisition of process data

Novel materials for organic optoelectronics

Ligands for the Nuclear Receptors LRH-1 and SF-1

Research group

Organic Chemistry: Synthesis, Catalysis and Flow

Affiliate research group

Centre of Excellence for Continuous Digital Chemical Engineering Science

Research project(s)

Whitby: Organic synthesis using transition metal chemistry

Whitby: Insertion of carbenoids into organozirconocene chlorides

Whitby: Natural product synthesis using zirconium chemistry

Whitby: Insertion of carbenoids into zirconacycles

Whitby: Synthesis of Bioactive compounds: Ligands for Nuclear Receptors and Neuroactive amines

Whitby: Invention of new transition metal catalysed reactions

Whitby: Asymmetric Synthesis - Novel chiral transition metal complexes

Nandhakumar & Whitby: Molecular Electronics and Neural Networks

Non-executive director of the Physical Sciences Database Service 

Advisory Board of the AI3SD Network+ (Artificial Intelligence and Augmented Intelligence for Automated Investigations for Scientific Discovery) 

Co-Director of the Centre of Excellence for Continuous Digital Chemical Engineering Science

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Key Publications

Articles

Book Chapter

Conferences

Letter/Editorial

Reports

Module Coordinator for CHEM2001 and  CHEM6158, and lecturer on CHEM3041 and CHEM2010.

Synthesis of Endohedral Fullerenes

Synthesis of fullerenes, such as C60, containing and endohedral species such as an inert gas atom, or small molecule such as H2, H2O, HF, and CH4, using a series of chemical reactions termed “Molecular Surgery”.

Compounds in which atoms or small molecules (A) are trapped in the cavity of fullerenes such as C60 are known as endofullerenes and denoted A@C60. They are of great interest for study of their material properties and the properties of the isolated endohedral species.

We synthesise endohedral fullerenes by a process termed ‘Molecular Surgery’ in which a series of chemical reactions is used to open a hole in a fullerene cage. The endohedral species is then inserted, often under pressure, then the hole closed to reform the original fullerene, but now enclosing the endohedral species. For example our synthesis of CH4@C601 (Figure, runner up for ‘Molecule of the Year’ in 20192) is shown in the Scheme.

Scheme: Molecular Surgery route to CH4@C60
Scheme: Molecular Surgery route to CH4@C60
Fig: CH4@C60.
Fig: CH4@C60.

We have developed improved methods for the synthesis of H2@C60, H2O@C603 which allow the large amounts of materials needed for spectroscopic studies, for example Inelastic Neutron Scattering, to be made. These molecules show quantum effects due to the interaction between nuclear spin (the H atoms may have the same or opposite spins) and quantised rotations.4 Remarkably the two types of water have different polarities.5

We extended the method to trap hydrofluoric acid inside C60 (HF@C60).6

Current interests include the inert gas fullerenes. We have made Ar@C607 and shown a remarkable coupling between the entrapped Helium nucleus and the cage in 3He@C60.8 Inert gas endofullerens are almost perfect examples of a ‘particle in box’ and spectroscopic determination of the quantised translational energy levels provide a powerful test for modern theories of non-bonding interactions. Other current targets include NH3@C60 (where the umbrella =inversion of ammonia, as used in the first MASERs is particularly interesting) and O2@C60 where the unpaired electrons on triplet state oxygen allow study by electron spin resonance.

1. Sally Bloodworth, Gabriela Sitinova, Shamim Alom, Sara Vidal, George R. Bacanu, Stuart J. Elliott, Mark E. Light, Julie M. Herniman, G. John Langley, Malcolm H. Levitt, Richard J. Whitby. First Synthesis and Characterization of CH4@C60, Angew. Chem Int Ed. 2019, 58, 5038-5043. DOI: 10.1002/anie.201900983

2. https://cen.acs.org/synthesis/CENs-molecules-year-2019/97/i48

3. A. Krachmalnicoff, M. H. Levitt, R. J. Whitby, "An optimised scalable synthesis of H2O@C60 and a new synthesis of H2@C60", Chem. Commun.,  2014, 50, 13037-13040.

4. S. Mamone, M. Concistre, E. Carignani, B. Meier, A. Krachmalnicoff, O. G. Johannessen, X. G. Lei, Y. J. Li, M. Denning, M. Carravetta, K. Goh, A. J. Horsewill, R. J. Whitby, M. H. Levitt, "Nuclear spin conversion of water inside fullerene cages detected by low-temperature nuclear magnetic resonance", J. Chem. Phys., 2014, 140, 194306. Benno Meier, Karel Kouril, Christian Bengs, Hana Kourilova, Timothy C barker, Stuart J Elliott, Shamim Alom, Richard J Whitby, Malcolm H Levitt, Spin-Isomer Conversion of Water at Room Temperature and Quantum-Rotor-Induced Nuclear Polarization in the Water-Endofullerene H2O@C60, Phys. Rev. Lett., 2018, 120, 26, 266001. DOI: 10.1103/PhysRevLett.120.266001.

5. Meier, S. Mamone, M. Concistre, J. Alonso-Valdesueiro, A. Krachmalnicoff, R. J. Whitby, M. H. Levitt, “Electrical detection of ortho-para conversion in fullerene-encapsulated water", Nature Commun.,  2015, 6, 8112. DOI:10.1038/ncomms9112.

6. Andrea Krachmalnicoff, Richard Bounds,  Salvatore Mamone,  Shamim Alom, Maria Concistrè, Benno Meier, Karel Kouřil, Mark E. Light, Mark R. Johnson, Stéphane Rols, Anthony J. Horsewill, Anna Shugai, Urmas Nagel, Toomas Rõõm, Marina Carravetta, Malcolm H. Levitt and Richard J. Whitby. The dipolar endofullerene HF@C60. Nature Chem., 2016, 8, 953-957.

7. S. Bloodworth, G. Hoffman, M. C. Walkey, G. R. Bacanu, J. M. Herniman, M. H. Levitt and R. J. Whitby.  Synthesis of Ar@C60 using molecular surgery.  Chem. Commun., 2020, 56, 10521-10524  DOI:10.1039/d0cc04201c

8. G. R. Bacanu, J. Rantaharju, G. Hoffman, M. C. Walkey, S. Bloodworth, M. Concistre, R. J. Whitby, M. H. Levitt, An Internuclear J-Coupling of 3He Induced by Molecular Confinement. J. Am. Chem. Soc. 2020, 142, 16926-16929. DOI:10.1021/jacs.0c08586

Organic Optoelectronics

Nuclear Receptors

Professor Richard J Whitby
Chemistry University of Southampton Highfield Southampton SO17 1BJ

Room Number: 30/3035

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