2026-04-05T11:49:29Zhttps://recercat.cat/oai/request
oai:recercat.cat:2445/1299632025-11-19T20:55:27Zcom_2072_1057col_2072_478917col_2072_478933
RECERCAT author Arlegui Chamizo, Aitor author El Hachemi, Zoubir author Crusats i Aliguer, Joaquim author Moyano i Baldoire, Albert 2019-03-08T13:09:30Z2019-03-08T13:09:30Z20182019-03-08T13:09:31Z 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. cc-by (c) Arlegui, Aitor et al., 2018 http://creativecommons.org/licenses/by/3.0/es info:eu-repo/semantics/openAccess Catàlisi heterogènia Sulfonació Reacció de Diels-Alder Heterogeneus catalysis Sulphonation Diels-Alder reaction 5-Phenyl-10,15,20-tris(4-sulfonatophenyl)porphyrin: Synthesis, catalysis and structural studies info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion