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

Abstract

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.

Publication DOI: https://doi.org/10.1021/acs.iecr.9b04105
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 https://doi.org/10.1021/acs.iecr.9b04105
Uncontrolled Keywords: Chemistry(all),Chemical Engineering(all),Industrial and Manufacturing Engineering
Publication ISSN: 1520-5045
Full Text Link:
Related URLs: https://pubs.ac ... 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.

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