UBC Theses and Dissertations
Azide substituted porphyrins with crosslinking applications for use in photodynamic therapy Fenwick, David
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.
Item Citations and Data