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EPSRC Reference: EP/C512049/1
Title: The Direct Heck Reaction On Porphyrins As A Novel Method For Introduction Of Beta-Substituents and Pi-Extension To Give New Chromophores
Principal Investigator: Cammidge, Professor AN
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: University of East Anglia
Scheme: Standard Research (Pre-FEC)
Starts: 01 October 2005 Ends: 30 September 2007 Value (£): 149,898
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Chemicals Pharmaceuticals and Biotechnology
Related Grants:
Panel History:  
Summary on Grant Application Form
Towards the end of another project (funded by The Leverhulme Trust) we made the remarkable discovery that intramolecular palladium catalysed (Heck) coupling could be achieved directly onto the porphyrin beta-positions. It is well known that, in any resonance form of porphyrins, two double bonds do not contribute to the overall aromatic system. Reduction (which preserves this aromaticity) to give chlorins is well known but no one has ever considered using these beta-positions as substrates for Heck coupling. The chemistry has enormous potential along both synthesis and materials paths. The intramolecular reactions lead to new, pi-extended planar porphyrins which will show favourable optical properties (red-shifted absorption). The intermolecular reaction offers a new and versatile method for introduction of beta-substituents. Use of blocking groups in the meso-positions could allow control over this substitution.
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