1230
Synthesis, Characterization, and Unusual Behavior of a Perfluoroarylated Fullerene

Tuesday, May 13, 2014: 08:00
Bonnet Creek Ballroom XI, Lobby Level (Hilton Orlando Bonnet Creek)
L. K. San, J. B. Whitaker (Colorado State University), A. A. Popov (IFW Dresden), S. H. Strauss, and O. V. Boltalina (Colorado State University)
Fullerenes and fullerene derivatives have attracted much attention due to their interesting optical and electronic properties. For example, further chemical elaborations of fullerenes possessing cyclo‐adducts (ie., phenyl‐C61‐butyric acid methyl ester, PCBM,1 and mono‐indene-C60, ICMA2) have shown promising use in photovoltaic energy conversion. Mono‐hydrofullerenes, C60RH, were shown as effective synthons for novel molecules3 with interesting physicochemical properties for various applications. The C‒H bond activation utilizing the acidic fullerenyl C60‒H proton can be realized by the use of strong bases. For instance, the dimerization of two RC60· radicals using NaOH in the presence of C60RH was used to form RC60‒C60R.4

In this work, we use the labile hydrogen atom on C60RH as a synthetic handle for further chemical elaborations, resulting in a novel perfluoroarylfullerene. One such product, a "fullerene-with-a-mohawk," was realized by the use of a base or by an one‐electron reductant. Products were characterized by 19F and 1H NMR spectroscopy, mass spectrometry, cyclic voltammetry, X‐ray crystallography, and DFT calculations.

References

(1)           Reyes-Reyes, M.; Kim, K.; Carroll, D. L. Appl. Phys. Lett. 2005, 87, 083506.

(2)           Coffey, D. C.; Larson, B. W.; Hains, A. W.; Whitaker, J. B.; Kopidakis, N.; Boltalina, O. V.; Strauss, S. H.; Rumbles, G. J. Phys. Chem. C 2012, 116, 8916.

(3)           Allard, E.; Cheng, F.; Chopin, S.; Delaunay, J.; Rondeau, D.; Cousseau, J. New J. Chem. 2003, 27, 188.

(4)           Lu, S.; Jin, T.; Bao, M.; Yamamoto, Y. Org. Lett. 2012, 14, 3466.