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Synthesis under high hydrostatic pressure — a new method to prepare 5,10,15,20-tetrakis[4-(substituted amino)-2,3,5,6-tetrafluorophenyl]porphyrins

Ana T.P.C. Gomes

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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Patrícia C. Freire

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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Catarina R.M. Domingos

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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Maria G.P.M.S. Neves

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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José A.S. Cavaleiro

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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Filipe A. Almeida Paz

Department of Chemistry, CICECO – Aveiro Institute of Materials, University of Aveiro, 3810-193 Aveiro, Portugal

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Jorge A. Saraiva

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

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, and

Augusto C. Tomé

Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal

E-mail Address: actome@ua.pt

Corresponding author; tel: +351 234-370-712

SPP full member in good standing

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https://doi.org/10.1142/S108842461650111XCited by:1 (Source: Crossref)

Abstract

5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin reacts with primary alkylamines and heterocyclic amines, at 50°C and under high pressure (450 MPa), to produce the $N$ $N$ -substituted tetraamino derivatives in high yields. Under similar conditions, the reaction with the bulky dibutylamine and dipentylamine affords the corresponding mono-substituted dialkylaminoporphyrins in 10% yield. This new protocol arises as a considerable improvement of the methods already known, which usually require high temperatures and are not effective when using secondary amines having long alkyl groups.

Dedicated to Professor Tomás Torres on the occasion of his 65th birthday

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