Combined Experimental and Computational Study of Polyaromatic Hydrocarbon Aggregation:Isolating the Effect of Attached Functional Groups


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 a combined experimental and computational approach. Containing alkoxy side chains of varying lengths or 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 and diffusion-ordered nuclear magnetic resonance spectroscopy, complemented with molecular dynamics simulations. There is a strong correlation between molecular architecture and aggregation mechanisms: the 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 structure-function relationship of polyaromatic hydrocarbons, such as asphaltenes, examined here over multiple length scales in a single solvent. We also demonstrate the importance of using complementary techniques to study the aggregation process of polyaromatic hydrocarbons that could form aggregates of various sizes over different time scales.

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Divisions: College of Engineering & Physical Sciences > School of Infrastructure and Sustainable Engineering > Chemical Engineering & Applied Chemistry
College of Engineering & Physical Sciences > Aston Institute of Materials Research (AIMR)
Additional Information: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Ind. Eng. Chem. Res., copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Uncontrolled Keywords: Chemistry(all),Chemical Engineering(all),Industrial and Manufacturing Engineering
Publication ISSN: 1520-5045
Last Modified: 04 Mar 2024 08:36
Date Deposited: 31 Oct 2019 09:57
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Related URLs: ... cs.iecr.9b04105 (Publisher URL)
http://www.scop ... tnerID=8YFLogxK (Scopus URL)
PURE Output Type: Article
Published Date: 2019-11-13
Accepted Date: 2019-10-01
Authors: Simionesie, Dorin
O’callaghan, Gregory
Laurent, Raphael
Preece, Jon A.
Evans, Robert (ORCID Profile 0000-0003-1471-201X)
Zhang, Zhenyu J.



Version: Accepted Version

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