Síntese de novos derivados fulerênicos explorando a "reação click" e de um derivado C60-catiônico polar

Abstract

The new carbon allotrope, the fullerene C60, since its discovery has generated great interest of the scientific community due to its unique properties and growing potential in the fields of materials and biology. However, the low solubility in organic solvents and its tendency togenerate aggregates limited fullerene applications. To minimize these properties, derivatization of fullerene C60 with organic compounds on its surface has being widely used by many research groups. This work was based on the synthesis of fullerene derivates exploiting Bingels cyclopropanation. Among the new synthesized fullerene derivatives,twelve were new, and one of these, made by eleven steps, is a cationic salt with solubility in polar solvents. Synthesis of functionalized glycoconjugated-fullerenes by using the known Click reactionwas explored in this work. Through this reaction, one molecule containing the azide function and other with alkyne functionality could be united to form the 1,2,3-triazol. This way, some monoadduct fullerene derivatives with the alkyne functionality were made to generate a building block. Later, these compounds would be used as starting material to react withother molecules containing the azide functionality. These new monoadduct fullerenes created to be a building block did not react by the Click reaction, probably due to their low solubility in organic solvents. After this, another bisadduct fullerene derivative was synthesized to form a new building block and overcome this issue. This compound turnedout to be a good substrate to the Click reaction, and after reacted with several carbohydrates containing azide functionality, six new fullero-glicoconjugates were made.