THE ROLE OF LOCAL AROMATICITY IN THE FLUORINATION PROCESS OF CARBON NANOTUBES Sílvia Osuna*1, Miquel Torrent-Sucarrat2, Christopher P. Ewels3, Miquel Solà1, Paul Geerlings2, Gregory Van Lier2
Institut de Quimica Computacional, Universitat de Girona, Campus Montilivi E-17071 Girona, Spain. Research Group of General Chemistry (ALGC), Vrije Universiteit Brussels, Pleinlaan 2, B-1050, Brussels, Belgium. 3 Institut des Matériaux Jean Rouxel, CNRS UMR6502, 2 rue de la Houssinière, 44322 Nantes, France. 1 2
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[email protected] In recent years, fluorination of nanotubes has been extensively studied as it provides an important and emerging process for functionalising and chemically activating carbon nanotube structures.1 However, the mechanisms of fluorine addition and the different patterns obtained are still an open issue. Aromaticity has already been shown to play a role in the fluorination of fullerenes and several studies have been reported concerning the aromaticity of carbon nanotubes.2 In this work, we have first examined the influence of nanotube curvature and length on the nucleus independent chemical shifts (NICS), and secondly the role of the aromaticity in the fluorination process of the nanotube surface.3 In particular, the influence of local aromaticity on the addition mechanism is discussed.4
Figure caption: NICS maps for pristine and 25% C4F fluorinated (6,6) carbon nanotube segment.
1
M. Glerup, V. Krstic, et al., Doped Nanomaterials and Nanodevices, Ed. W. Chen, American Scientific Publishers, 2007. 2 (a) Ormsby, J.L.; King, B. T. J. Org. Chem. 2004, 69, 4287 (b) Matsuo, Y.; Taharo, K.; Nakamura, E. Org. Lett. 2003, 5, 3181 (c) Bauschlicher Jr, C.W. Chem. Phys. Lett. 2000, 322, 237 (d) Zhao, J.; Balbuena, P.B. J. Phys. Chem. C 2008, 112, 3482. 3 Osuna, S.; Torrent-Sucarrat, M.; Ewels, C. P.; Solà, M.; Geerlings, P.; Van Lier, G. Submitted for publication. 4 (a) Ewels, C.P.; Van Lier, G.; Charlier, J.-C.; Heggie, M.I.; Briddon, P.R. Phys. Rev. Lett. 2006, 96, 216103. (b) Osuna, S.; Ewels, C. P.; Torrent-Sucarrat, M.; Solà, M.; Geerlings, P.; Van Lier, G. In preparation.
