## 3 Results and Discussion  
### Synthesis and Structural Characterization of Benztriimidazole Materials  
A family of benzotriimidazole-based materials was synthesized using a condensation reaction between \(N^{1}\),\(N^{3}\),\(N^{5}\)-triphenylbenzene-1,2,3,4,5,6-hexaamine and selected acyl chlorides. The synthetic procedure is shown below. Initially, condensation of \(N^{1}\),\(N^{3}\),\(N^{5}\)-triphenylbenzene-1,2,3,4,5,6-hexaamine with a selected acyl chloride was carried out in a solvent of \(N\)-methyl-2-pyrrolidone in a single step. In an effort to improve the ratio of products, the reaction was also studied using a variety of other solvents, including acetic acid, acetic anhydride, and phosphoryl chloride, based on precedents from the literature. Despite varying the solvent, the reaction reliably produced a mixture of products with the desired benzotriimidazole material consisting of roughly one third of the mixture. The condensation reaction has competing synthetic pathways which result in roughly two thirds of the product mixture consisting of undesired pseudo-para benzodiimidazole. The competing condensation pathways for benzotriimidazole versus benzodiimidazole are depicted below. A similar problem was also encountered by [PERSON] et al. [25] with yields of their tris(aroyleneimidazole). They reported similar competing reaction pathways that resulted in far more bis(aroyleneimidazole) in their product mixture. One commonly-reported strategy to improve the yield for the synthesis of benzimidazoles is a two-step condensation reaction [26]. This strategy was adapted to the benzotriimidazole synthesis to improve the overall yield, as well as to improve the ratio of the product mixture in favor of the desired triple-condensed product. As the initial step, three equivalents of acyl chloride were added to \(N^{1}\),\(N^{3}\),\(N^{5}\)-triphenylbenzene-1,2,3,4,5,6-hexaamine and stirred at room temperature in DMF (Dimethyl Formamide) for 90 min before precipitation into water to isolate the condensation intermediate. Cyclization of the condensation intermediate was tested in a variety of reaction conditions in an effort to change the product ratio away from favoring pseudo-para benzodiimidazole. Solvents and reaction temperature were varied, the intermediate was also added to the refluxing solvent to avoid slowly heating the intermediate from room temperature in case that process was the root of pseudo-para benzodiimidazole formation. Despite great effort to improve the yield of the benzotriimidazole, only marginal improvements were made by utilizing the two-step condensation procedure. As a result, larger scale reactions were carried out in a single-step condensation. After condensation, the benzotriimidazole reaction mixture was precipitated into water and the crude product was isolated by filtration. Small-scale reactions were purified by silica gel column chromatography to separate the desired benzotriimidazole from the benzodiimidazole. To save time and solvent, larger scale reactions were purified by Soxhlet extraction. The isolated yields for the six different benzotriimidazole molecules range from 27-33%. The six synthetic examples of benzotriimidazole materials (Figure 2) are as follows:Synthesis of 2,5,8-tris(4-_tert_-butyl-phenyl)-1,4,7-triphenyl-4,7-dihydro-1\(H\)-benzo[1,2-\(d\):3,4-\(d^{\prime}\):5,6-\(d^{\prime\prime}\)]triimidazole (Tris butyl). \(N^{1}\),\(N^{3}\),\(N^{5}\)-triphenylbenzene-1,2,3,4,5,6-hexaamine (2.0 g 5 mmol) and 4-_tert_-butyl-benzoylchloride (3.14 g, 16 mmol) were dissolved in anhydrous \(N\)-methyl-2-pyrrolidone (30 mL). The resulting mixture was stirred at room temperature for one hour. The reaction mixture was refluxed for 16 h and then, after cooling to room temperature, was precipitated in 500 mL of water and filtered to isolate the brown precipitate as a crude product. The brown solid was purified by silica gel column chromatography with an eluent of 20% ethyl acetate and 80% hexane.