Upon analysis of these condensation trials of unfunctionalized phthalocyanine, it was hypothesized that the solubility of the precursor silanol, the imparted steric hinderance of the chosen triisopropylsiloxy-functional group, and the strength of silicon-oxygen bonding led to preferential functionalization of the phthalocyanine precursor. Under this understanding, the silanol is not only more likely to achieve a favorable collision to bond to the siloxy-backbone but also sterically obstructs the site. To investigate the effect of functional group steric hinderance and bond strength in the dimerization of a functionalized silicon phthalocyanine precursor, a novel triethylgerminol compound was synthesized and characterized both by IR (Figure ) and 1 H NMR (Figure ) spectroscopy techniques. Utilizing this synthesized germinal, a series of concerted functionalization-dimerization trials were performed. After a 3.5-hour and 24-hour trial demonstrated the presence of only monomeric germoxysilicon phthalocyanine in the product worked up using vacuum filtration, the reaction was reattempted using dry 2,6-lutidine to wash the product and a filter pipette in place of vacuum filtration to avoid contamination of the sample with atmospheric condensation.