Sustainable Approaches to the Synthesis of Metallophthalocyanines in Solution
| Autor: | Patrizia Imperatori, Anna Maria Paoletti, Giovanna Pennesi, Gloria Zanotti |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Metal ions in aqueous solution
Inorganic chemistry Pharmaceutical Science chemistry.chemical_element Zinc Article Analytical Chemistry lcsh:QD241-441 Metal chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery Glycerol Reactivity (chemistry) metallomacrocycles Physical and Theoretical Chemistry Potassium hydroxide Organic Chemistry sustainability Anisole chemistry Chemistry (miscellaneous) Yield (chemistry) visual_art visual_art.visual_art_medium Molecular Medicine alternative solvents |
| Zdroj: | Molecules Volume 26 Issue 6 Molecules, Vol 26, Iss 1760, p 1760 (2021) Molecules (Basel, Online) (2021). doi:10.3390/molecules26061760 info:cnr-pdr/source/autori:Gloria Zanotti, Patrizia Imperatori, Anna Maria Paoletti, Giovanna Pennesi/titolo:Sustainable Approaches to the Synthesis of Metallophthalocyanines in Solution/doi:10.3390%2Fmolecules26061760/rivista:Molecules (Basel, Online)/anno:2021/pagina_da:/pagina_a:/intervallo_pagine:/volume |
| ISSN: | 1420-3049 |
| Popis: | This work aims to investigate more sustainable reaction conditions for the synthesis of metallophthalocyanines. Anisole, glycerol and their mixtures have been investigated as reaction media for the tetramerization of phthalonitriles. Acetates of three divalent first-transition metal cations, Co(II), Cu(II) and Zn(II), were used and several bases were tested, depending on the chosen substrates and reaction conditions, with a view to making the whole process more sustainable while ensuring its scalability. Unsubstituted phthalocyanines were synthesized to analyze the behavior of the different metal ions in terms of reactivity in the new reaction media, resulting in a general Cu > Co > Zn trend, while the nonpolar tetra-tert-butyl substitution was investigated to evaluate the synthesis of soluble derivatives in the new conditions. Furthermore, the potassium hydroxide (KOH)-aided statistical synthesis of the unsymmetrical 9(10), 16(17), 23(24)-tri-tert-butyl-2-iodophthalocyaninato zinc(II), starting from 4-tert-butylphthalonitrile and 4-iodophthalonitrile in a glycerol/anisole mixture, proceeded with a satisfactory 26% yield. Our results provide insights into the investigation of new reaction environments and the understanding of their strengths and weaknesses, with a view to further increasing the sustainability of the synthesis of metallomacrocycles with high added value while lowering their production cost. |
| Databáze: | OpenAIRE |
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