Síntese de fulerenos funcionalizados com potencial atividade antioxidante

Abstract

The C60 fullerene is, among the clusters of carbon, the most studied and detailed information about its structure and reactivity are well known to date. Because of its unique properties such as superconductivity, ferromagnetism, photoreactivity, electroluminescence, and biological effects, the fullerene C60 has caused strong interest in the scientific community at the past twenty years. However, to exploit their interesting properties is necessary, in most cases, solubilize it in usual solvents, that ideally can be obtained by chemical functionalization. This work aimed at functionalizing C60 fullerene through the Bingel´s cyclopropanation or by Prato´s pyrrolidine ring reaction, generating compounds known as fulleropyrrolidines. Several malonamides were studied as starting materials for cyclopropanation, diverging of classic reaction and giving innovative nature to the present work. The Prato´s reaction was carried out in order to obtain a fuleropyrrolidine alkyne key intermediate that could be used in cycloaddition like the well-known "click" reaction. Finally, a study for developing novel synthetic route of 5-aminolevulinic acid, an important compound used in photodynamic therapy (PDT), was also performed.