With the goal of creating a porphyrin we reacted isoquinol pyrrole, p-fluorobenzaldehyde, and boron trifluoride etherate under appropriate conditions. Instead of a porphyrin being synthesized, we created polyisoquinol pyrrole in high yield and with great absorption properties around 600nm. We characterized this compound via UV/vis spectroscopy, proton NMR, and electrochemistry. The compound was then reacted with [Ru(bipy)2Cl2] to create a cationic compound and this molecule was tested as a possible photosensitizer for photodynamic therapy (PDT) but it was unable to photocleave plasmid DNA above 550nm. The original compound was then methylated and this new compound was also tested as a photosensitizer. This complex was successful at photocleaving DNA above 550nm and appears to be a promising photosensitizer.
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Chemistry | Physical Sciences and Mathematics
Versteeg, Gregory, "Photoreactions of a Water Soluble Poly-isoquinolpyrrole with Plasmid DNA" (2014). Honors Theses. 6.