Ultra-Fast Dendritic Growth Based on the Grafting of Fullerene Hexa-Adduct Macromonomers onto a Fullerene Core

A fullerene hexa‐adduct building block bearing an azide functionality was prepared in six steps, and grafted onto a central fullerene core under copper‐catalyzed azide–alkyne cycloaddition conditions. The resulting tridecafullerene derivative is a first generation dendrimer with 132 peripheral ethyl...

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Veröffentlicht in:European journal of organic chemistry 2016-06, Vol.2016 (16), p.2882-2887
Hauptverfasser: Sigwalt, David, Caballero, Rubén, Holler, Michel, Strub, Jean-Marc, Van Dorsselaer, Alain, Nierengarten, Jean-François
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Sprache:eng
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Zusammenfassung:A fullerene hexa‐adduct building block bearing an azide functionality was prepared in six steps, and grafted onto a central fullerene core under copper‐catalyzed azide–alkyne cycloaddition conditions. The resulting tridecafullerene derivative is a first generation dendrimer with 132 peripheral ethyl ester groups. This compound was characterized by different spectroscopic techniques (1H and 13C NMR, IR, UV/Vis), and by MALDI‐TOF mass spectrometry. Despite a high degree of fragmentation, the molecular‐ion peak was detected, and all the observed fragments originate from a fully clicked derivative. This shows that the construction of dendrimers in a single dendritic growth step from fullerene hexa‐adduct macromonomers is an efficient strategy to produce monodisperse compounds. A fullerene hexa‐adduct building block bearing an azide functionality was prepared in six steps, and grafted onto a central fullerene core under copper‐catalyzed azide–alkyne cycloaddition conditions. The resulting tridecafullerene derivative is a first generation dendrimer with 132 peripheral ethyl ester groups.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600439