From conventional to microphotochemistry: A study of phthalimide and phthalonitrile derivatives
Gallagher, Sonia (2011) From conventional to microphotochemistry: A study of phthalimide and phthalonitrile derivatives. PhD thesis, Dublin City University.
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This research explores the application of synthetic organic photochemistry for the preparation of new phthalimide and phthalonitrile derivatives. Photodecarboxylative (PDC) additions of carboxylates to phthalimides were explored, this work included addition reactions using phenyl acetates, α-keto carboxylates and protected amino acids. Once these photo-additions were optimised using a Rayonet reactor, interest was turned to the conversion of this chemistry to a micro-flow platform with a view to improving the results obtained using the large-scale Rayonet reactor. It was successfully demonstrated that the microreactor delivered comparable if not superior results.
The possibility of using the PDC addition products as precursors for the synthesis of aristolactams was investigated. Optimisation of a method for the preparation of several compounds related to the aristolactam family was attempted, with the successful preparation of two compounds achieved. Also described is the photochemical synthesis of new phosphorescent phthalonitrile derivatives and their respective phthalocyanines. Two of the phthalonitrile derivatives were successfully converted to water soluble derivatives by selective sulfonation and one such derivative was screened as a potential cell-imaging agent.
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