Aggregation of asphaltene model compounds using a porphyrin tethered to a carboxylic acid

A Ni(II) porphyrin functionalized with an alkyl carboxylic acid (3) has been synthesized to model the chemical behavior of the heaviest portion of petroleum, the asphaltenes. Specifically, porphyrin 3 is used in spectroscopic studies to probe aggregation with a second asphaltene model compound conta...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-07, Vol.13 (25), p.6984-6991
Main Authors: Schulze, Matthias, Lechner, Marc P, Stryker, Jeffrey M, Tykwinski, Rik R
Format: Article
Language:English
Subjects:
Alkylation
Carboxylic Acids - chemistry
Dimerization
Magnetic Resonance Spectroscopy
Nickel - chemistry
Petroleum - analysis
Polycyclic Aromatic Hydrocarbons - chemistry
Porphyrins - chemistry
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Summary:A Ni(II) porphyrin functionalized with an alkyl carboxylic acid (3) has been synthesized to model the chemical behavior of the heaviest portion of petroleum, the asphaltenes. Specifically, porphyrin 3 is used in spectroscopic studies to probe aggregation with a second asphaltene model compound containing basic nitrogen (4), designed to mimic asphaltene behavior. NMR spectroscopy documents self-association of the porphyrin and aggregation with the second model compound in solution, and a Job's plot suggests a 1 : 2 stoichiometry for compounds 3 and 4.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00836k