Nanoaggregation of Polyaromatic Compounds Probed by Electrospray Ionization Mass Spectrometry

Liu, Lan; Sjöblom, Johan; Xu, Zhenghe

doi:10.1021/acs.energyfuels.5b02390

Cited by 5 publications

(19 citation statements)

References 49 publications

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“…It appears that the level of nanoaggregation is much more sensitive to concentration for C5Pe than for C5PeC11. 34 The effect of heptane addition on nanoaggregation of C5PeC11 was investigated by adding a varying amount of heptane into 10 µM C5PeC11 solutions. The results in Figure 3 nanoaggregates with n=5~8 were observed when adding heptane, the dominant nanoaggregation level for C5PeC11 was still dimers and trimers.…”

Section: Nanoaggregation Of Synthetic Polyaromatic Compoundsmentioning

confidence: 99%

Interactions of Polyaromatic Compounds. Part 1: Nanoaggregation Probed by Electrospray Ionization Mass Spectrometry and Molecular Dynamics Simulation

Liu

Zhang

et al. 2017

Energy Fuels

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Nanoaggregation of three synthetic polyaromatic compounds, N-(1-hexylhepyl)-N'-(5carboxylicpentyl)-perylene-3, 4, 9, 10-tetracarboxilicbisimide (C5Pe), N-(1-undecyldodecyl)-N'-(5-carboxylicpentyl)-perylene-3,4,9,10-tetracarboxylbisimide (C5PeC11) and N,N'-bis(1undecyldodecyl)perylene-3,4,9,10-tetracarboxylbisimide (BisAC11) individually or in their binary mixtures was studied under various solution conditions using electrospray ionization mass spectrometry (ESI-MS) and molecular dynamics (MD) simulation. The results from ESI-MS showed a significant enhancement in nanoaggregation of each individual component by increasing their concentration or heptane addition to toluene. Mixing a polyaromatic compound of longer aliphatic chain with a shorter chain polyaromatic compound in a given solvent was found to reduce the apparent average nanoaggregation number significantly. Replacing the-COOH group with an aliphatic group induced further steric hindrance to nanoaggregation of polyaromatic cores in the mixture. The results from MD simulations showed a similar trend of reducing nanoaggregation by mixing of two different polyaromatic compounds. The results of MD simulation further revealed that π-π stacking between polyaromatic cores is the major driving force for nanoaggregation while steric repulsion and strong solvation of longer aliphatic chains connected to the polyaromatic core hinder nanoaggregation of polyaromatic compounds studied. The results from this study provide a scientific basis for controlling nanoaggregation of polyaromatic compounds and shed lights on understanding the observed aggregation of asphaltenes in crude oil.

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Section: Nanoaggregation Of Synthetic Polyaromatic Compoundsmentioning

confidence: 99%

Interactions of Polyaromatic Compounds. Part 1: Nanoaggregation Probed by Electrospray Ionization Mass Spectrometry and Molecular Dynamics Simulation

Liu

Zhang

et al. 2017

Energy Fuels

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“…The self-assembly of π-conjugated organic molecules has always been an active research topic, due to its high thermal stability and photostability at ambient conditions, which make its applications in optoelectronic attractive. The property of easy chemical modification by various functional groups promotes the formation of well-defined nanostructures fabricated by PBIs, and inspires the research on self-assembly of n-type organic semiconductor molecules. , As a result, increasingly more efforts have been devoted to expanding the possible applications of PBIs. , …”

Section: Introductionmentioning

confidence: 99%

“…Sjöblom’s group designed and synthesized a series of model compounds of asphaltenes. These model compounds are derivatives of perylene imide molecules with alkyl chains and polar groups attached to the polyaromatic core. − Great efforts have been made to understand interfacial behaviors of these model compounds. − …”

Section: Introductionmentioning

confidence: 99%

“…1,2 As a result, increasingly more efforts have been devoted to expanding the possible applications of PBIs. 3,4 Asphaltenes are the most aromatic of the largest, densest and heaviest components with remarkable surface-active properties in crude oil. They are defined as a solubility class, not by their structure, i.e., insoluble in alkanes such as pentane or heptane, but soluble in aromatic solvents such as toluene or xylene.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synergistic Adsorption of Polyaromatic Compounds on Silica Surfaces Studied by Molecular Dynamics Simulation

Xiong

Cao

et al. 2018

J. Phys. Chem. C

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Adsorption on silica surfaces of polyaromatic compounds, N-(1-hexylhepyl)-N′-(5-carboxylicpentyl)-perylene-3,4,9,10-tetracarboxylic bisimide (C5Pe) and N-(1-undecyldodecyl)-N′-(5-carboxylicpentyl)-perylene-3,4,9,10-tetracarboxylic bisimide (C5PeC11), individually and their binary mixture in heptol (mixture of heptane and toluene as oil) solutions were studied by molecular dynamics (MD) simulation, quartz crystal microbalance with dissipation (QCM-D), and atomic force microscopy (AFM). The MD simulation results showed that C5Pe molecules tend to aggregate and form a large cluster rapidly in the oil phase, reducing the energy of the system. In contrast, C5PeC11 molecules with higher solubility tend to disperse in the system. As a result, C5PeC11 molecules exhibited a stronger adsorption than C5Pe molecules on silica surfaces. In the binary mixture system, the overall solubility is only slightly lower than that in the C5PeC11 system due to the association of C5Pe with C5PeC11 molecules through π–π stacking and T-stacking interactions, leading to more polyaromatic compounds available for adsorption onto silica surfaces. The enhanced adsorption of both polyaromatic compounds on silica surfaces clearly illustrates the synergy of adsorption in the mixed systems of C5Pe and C5PeC11 as compared with the systems of their individual species. The adsorption characteristics revealed in MD simulations were confirmed by QCM-D measurement and AFM imaging. The observed synergy of adsorption provides insights into molecular assembly at silica–oil interfaces for the fabrication of devices or sheds lights on petroleum processing.

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“…18 To elucidate the specific influence of functional groups and chemical structures on the aggregation process of asphaltene, one approach is to develop model polyaromatic compounds with well-controlled structure, mimicking that of natural asphaltene. [20][21][22][23] A model system that can be studied by both experimental and computational methods offers significant advantage in establishing how molecular structures determine clustering behaviour. 20 A recent study investigated the structural and compositional aspects of asphaltenes by comparing the aggregation behaviour of continental, archipelago, and anionic continental model asphaltenes using molecular simulations.…”

Section: Introductionmentioning

confidence: 99%

Clustering behaviour of polyaromatic compounds mimicking natural asphaltenes

Simionesie

O'Callaghan

Costa

et al. 2020

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Clustering behaviour of hexa-tert-butylhexa-peri-hexabenzocoronene (HTBHBC) and its derivatives has been used as a model system to mimic that of natural asphaltenes. We used light scattering and 1 H-NMR spectroscopy, complemented by molecular dynamics simulation, to examine HTBHBC and its derivatives in toluene and toluene/heptane mixture, over a range of concentrations. The dispersibility of HTBHBC in toluene was found to be strongly dependent on its concentration. At concentrations below 5 mg/mL, HTBHBC appears to be fully dispersed and clustering equilibrium was reached within minutes as shown by scattering intensity measurements. At greater concentrations, the scattering intensity was approximately similar for all concentrations initially, but then decreased very slowly towards an apparent clustering equilibrium within two weeks. The mean hydrodynamic diameter of clusters, measured by dynamic light scattering, was initially around 1 micron for all concentrations greater than 5 mg/mL and then gradually reduced to around 0.4 micron at clustering equilibrium. At concentrations of 10 mg/mL and above, solid deposits were observed in toluene solutions when equilibrium was reached. 1 H-NMR spectroscopy showed that the precipitate was high purity HTBHBC possessing a planar structure, while the liquid phase contained a mixture of planar HTBHBC and its non-planar derivatives, forming colloidal clusters. The results show that the clustering process of asphaltene mimics in toluene can be extremely slow and great care should be taken when preparing equilibrated solutions. We also showed that observations of the solid-liquid equilibrium and clustering behaviour can be strongly dependent on the molecular structure of the polyaromatic compounds found in natural asphaltenes, and the structural and compositional evolution of colloidal clusters following an initial dispersion of asphaltene mimics in solvents.

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Nanoaggregation of Polyaromatic Compounds Probed by Electrospray Ionization Mass Spectrometry

Cited by 5 publications

References 49 publications

Interactions of Polyaromatic Compounds. Part 1: Nanoaggregation Probed by Electrospray Ionization Mass Spectrometry and Molecular Dynamics Simulation

Interactions of Polyaromatic Compounds. Part 1: Nanoaggregation Probed by Electrospray Ionization Mass Spectrometry and Molecular Dynamics Simulation

Synergistic Adsorption of Polyaromatic Compounds on Silica Surfaces Studied by Molecular Dynamics Simulation

Clustering behaviour of polyaromatic compounds mimicking natural asphaltenes

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