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Microwave‐Assisted Functionalization of Carbon Nanostructures in Ionic Liquids
Author(s) -
Guryanov Ivan,
Toma Francesca Maria,
Montellano López Alejandro,
Carraro Mauro,
Da Ros Tatiana,
Angelini Guido,
D'Aurizio Eleonora,
Fontana Antonella,
Maggini Michele,
Prato Maurizio,
Bonchio Marcella
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901408
Subject(s) - ionic liquid , surface modification , fullerene , tetrafluoroborate , carbon nanotube , cycloaddition , materials science , selectivity , carbon fibers , ionic bonding , chemistry , organic chemistry , nanotechnology , ion , catalysis , composite number , composite material
The effect of microwave (MW) irradiation and ionic liquids (IL) on the cycloaddition of azomethine ylides to [60]fullerene has been investigated by screening the reaction protocol with regard to the IL medium composition, the applied MW power, and the simultaneous cooling of the system. [60]Fullerene conversion up to 98 % is achieved in 2–10 min, by using a 1:3 mixture of the IL 1‐methyl‐3‐ n ‐octyl imidazolium tetrafluoroborate ([omim]BF 4 ) and o ‐dichlorobenzene, and an applied power as low as 12 W. The mono‐ versus poly‐addition selectivity to [60]fullerene can be tuned as a function of fullerene concentration. The reaction scope includes aliphatic, aromatic, and fluorous‐tagged (FT) derivatives. MW irradiation of IL‐structured bucky gels is instrumental for the functionalization of single‐walled carbon nanotubes (SWNTs), yielding group coverages of up to one functional group per 60 carbon atoms of the SWNT network. An improved performance is obtained in low viscosity bucky gels, in the order [bmim]BF 4 > [omim]BF 4 > [hvim]TF 2 N (bmim=1‐methyl‐3‐ n ‐butyl imidazolium; hvim=1‐vinyl‐3‐ n ‐hexadecyl imidazolium). With this protocol, the introduction of fluorous‐tagged pyrrolidine moieties onto the SWNT surface (1/108 functional coverage) yields novel FT‐CNS (carbon nanostructures) with high affinity for fluorinated phases.