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Open AccessArticle

5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies

1
Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, University of Barcelona, Faculty of Chemistry, Carrer de Martí i Franquès 1-11, 08028 Barcelona, Catalonia, Spain
2
Institute of Cosmos Science, Carrer de Martí i Franquès 1-11, 08028 Barcelona, Catalonia, Spain
*
Authors to whom correspondence should be addressed.
Academic Editors: M. Graça P. M. S. Neves, M. Amparo F. Faustino and Nuno M. M. Moura
Molecules 2018, 23(12), 3363; https://doi.org/10.3390/molecules23123363
Received: 29 November 2018 / Revised: 17 December 2018 / Accepted: 18 December 2018 / Published: 19 December 2018
A convenient protocol for the preparation of 5-phenyl-10,15,20-tris(4-sulfonatophenyl)porphyrin, a water-soluble porphyrin with unique aggregation properties, is described. The procedure relies on the one-pot reductive deamination of 5-(4-aminophenyl)-10,15,20-tris(4-sulfonatophenyl)porphyrin, that can be in turn easily obtained from 5,10,15,20-tetraphenylporphyrin by a known three-step sequence involving mononitration, nitro to amine reduction and sulfonation of the phenyl groups. This method provides the title porphyrin in gram scale, and compares very favorably with the up to now only described procedure based on the partial sulfonation of TPP, that involves a long and tedious chromatographic enrichment of the final compound. This has allowed us to study for the first time both the use of its zwitterionic aggregate as a supramolecular catalyst of the aqueous Diels–Alder reaction, and the morphology of the aggregates obtained under optimized experimental conditions by atomic force microscopy and also by transmission electron cryomicroscopy. View Full-Text
Keywords: azotization; heterogeneous catalysis; cryo-TEM; deamination; Diels-Alder reaction; PFM imaging; porphyrin aggregates; porphyrin synthesis; reduction; sulfonation; water-soluble porphyrin azotization; heterogeneous catalysis; cryo-TEM; deamination; Diels-Alder reaction; PFM imaging; porphyrin aggregates; porphyrin synthesis; reduction; sulfonation; water-soluble porphyrin
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MDPI and ACS Style

Arlegui, A.; El-Hachemi, Z.; Crusats, J.; Moyano, A. 5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies. Molecules 2018, 23, 3363.

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