Synthesis and Aggregation Behavior of Chiral Naphthoquinoline Petroporphyrin Asphaltene Model Compounds

Schulze M, Scherer A, Hampel F, Stryker JM, Tykwinski R (2016)

Publication Status: Published

Publication Type: Journal article, Original article

Publication year: 2016

Journal

Publisher: Wiley-VCH Verlag

Book Volume: 22

Pages Range: 3378-3386

Journal Issue: 10

DOI: 10.1002/chem.201504683

Abstract

The synthesis of structurally relevant compounds that model the chemical behavior and supramolecular aggregation of the asphaltenes, the most polar and metal-rich fraction of heavy petroleum, has been extended to include fusions of important petroleum biomarkers. The synthetic protocol features a multicomponent reaction to form a dyad composed of a fused steroidal naphthoquinoline, followed by a pyrrole cyclocondensation reaction to incorporate the dyad into a chiral triad containing a Ni-porphyrin substituent. This synthetic protocol has been used to prepare large molecules that represent both "continental" and "archipelago" models of asphaltene composition. The steroid-naphthoquinoline-porphyrin triads have been studied by UV/Vis and circular dichroism (CD) spectroscopies, and the results suggest that the naphthoquinoline core, a tetrahydro[4]helicene, adopts a helical conformation, producing a CD signal electronically related to the characteristic Soret absorption band of the porphyrin subunit. Finally, supramolecular aspects of asphaltene aggregation have been examined on a molecular level through analysis of axial coordination of pyridine to the Ni-porphyrin. The relative affinity of pyridine for binding to the Ni center of the porphyrin is evaluated by comparing binding propensities in a series of sterically differentiated substituted porphyrins.

Authors with CRIS profile

Involved external institutions

University of Alberta Canada (CA)

How to cite

APA:

Schulze, M., Scherer, A., Hampel, F., Stryker, J.M., & Tykwinski, R. (2016). Synthesis and Aggregation Behavior of Chiral Naphthoquinoline Petroporphyrin Asphaltene Model Compounds. Chemistry - A European Journal, 22(10), 3378-3386. https://doi.org/10.1002/chem.201504683

MLA:

Schulze, Matthias, et al. "Synthesis and Aggregation Behavior of Chiral Naphthoquinoline Petroporphyrin Asphaltene Model Compounds." Chemistry - A European Journal 22.10 (2016): 3378-3386.

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