To establish, and isolate, the influence of different chemical functional groups on the aggregation of polyaromatic hydrocarbons, a series of triphenylene-based compounds were investigated using experimental and computational approaches together. Containing alkoxy-side chains of varying length and amide appendages, both with and without a terminating carboxylic acid, their aggregation structures, sizes, and kinetics in toluene were studied over several length scales, using a combination of Dynamic Light Scattering (DLS) and Diffusion-Ordered NMR spectroscopy (DOSY), complemented with Molecular Dynamics (MD) simulations. There is a strong correlation between molecular architecture and aggregation mechanisms across different length scales: addition of polar functional groups and heteroatoms resulted in compounds that are more prone to aggregation and form large, micrometer-sized clusters, while the increased steric hindrance imposed by alkoxy-side chains led to stable nanometer-sized aggregates. These conclusions underline the strong structurefunction relationship of polyaromatic hydrocarbons, such as asphaltenes, examined here over multiple size-scales in a single solvent. We also demonstrated the importance of using complementary techniques to study the aggregation process of polyaromatic hydrocarbons that could form aggregates of various sizes over different timescales.
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