Initial dimerization trials of unfunctionalized monomeric silicon phthalocyanine were modeled after dehydration polymerizations. Four total reactions were attempted at run times of 1.5, 3.5, 24, and 48 hours. The 1 H NMR spectrum of the product resulting from a functionalized silicon phthalocyanine 3.5-hour condensation trial is shown in Figure . The ring proton pair in the 8.0-10.0 ppm region with <1.0 ppm peak separation indicates minimal amounts of the target dimeric phthalocyanine product present in the sample. Meanwhile, the ring proton pair in the 8.0-10.0 ppm region with >1.0 ppm peak separation is indicative of the undesired monomeric species. While this trial demonstrated the greatest proportion of dimeric species detected via NMR spectroscopy, low yield rendered it not viable for the pursuit of a sample for X-ray crystallography.