A series of alkynylated porphyrin and bacteriochlorin compounds were synthesized in good yields and characterized using NMR. The alkyne group affords a valuable synthetic handle for a variety of reactions including 1,3-dipolar cycloaddition reactions. Two strategies (pre- and post-functionalization) were employed to introduce alkyne moieties at different positions on the   porphyrin or bacteriochlorin macrocycle.  The “pre-functionalization strategy” used classic condensation methods with alkyne-containing starting materials to create aryl-substituted porphyrins. Secondly, a “post-functionalization” method utilized the palladium-catalyzed Sonogashira reaction of a “meso”-brominated porphyrin or bacteriochlorin to install the alkyne group.  These functionalized porphyrin and bacteriochlorin compounds are particularly interesting for their potential use as a photosensitizer for solar cells and a cancer therapy known as photodynamic therapy.

Synthesis and characterization of alkynylated porphyrins and bacteriochlorins

251st National Meeting (2016)

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