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Azide substituted porphyrins with crosslinking applications for use in photodynamic therapy Fenwick, David

Abstract

The objective of this work was to synthetically modify porphyrins such that they would possess a photoactive functionality which would chemically crosslink upon photoactivation for use in photodynamic therapy. Three novel azide-modified porphyrins (77, 86 and 101) were synthesised, isolated and characterised. These were investigated for their ability to extrude N₂ on thermal and/or photochemical activation. Upon activation of 77, the aldehyde (39) was formed. [Diagram] Activation of 86 led to a complex mixture where no pure compounds could be isolated or characterised. [Diagram] Activation of 101 gave a triplet derived product (103) in toluene, and a singlet derived product (104) when activated in mesitylene. [Diagram] The synthesis toward meso-azido porphyrins as well as diazirine-modified porphyrins were also carried out during the course of this work.

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