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Synthesis of AC60-Para-Xylylene Copolymer

Published online by Cambridge University Press:  25 February 2011

Douglas A. Loy  and
Roger A. Assink
Douglas A. Loy
Affiliation:
Fuel Science Department 6211 and Physical Chemistry and Mechanical Properties of Polymers Department 1812 Sandia National Laboratories, Albuquerque, NM 87185
Roger A. Assink
Affiliation:
Fuel Science Department 6211 and Physical Chemistry and Mechanical Properties of Polymers Department 1812 Sandia National Laboratories, Albuquerque, NM 87185
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Abstract

The preparation and purification of macroscopic quantities of buckminsterfullerenes [1] or buckyballs has ignited an explosion of research into their physical and chemical properties, and a variety of strategies for preparing new fullerene-based materials. Free radical synthesis is an appealing approach for forming polymeric fullerene materials. We report a polymeric fullerene material prepared by reacting pure C60 with xylylene from the thermolysis of paracyclophane. Addition of xylylene to a purple solution of C60 in toluene solution at -78 °C resulted in an olive-green solution from which an insoluble brown powder precipitated upon warming to room temperature. Analyses of the powder by solid state 13C MAS NMR, IR, and thermal gravimetric analysis are consistent with C60-xylylene copolymer.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 247: Symposium N – Electrical, Optical, and Magnetic Properties of Organic Solid State Materials , 1992 , 355
Copyright
Copyright © Materials Research Society 1992

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References

REFERENCES

[1] a) Kratschmer, W., Fostiropoulos, K., Huffman, D.R., Chem. Phys. Lett., 170, 167, (1990).Google Scholar
b) Kratschmer, W., Lamb, L.D., Fostiropoulos, K., Huffman, D.R., Nature, 347, 354, (1990).Google Scholar
c) Haufler, R.E., Conceicao, J., Chibante, L.P.F., Chai, Y., Byrne, N.E., Flanagan, S., Haley, M.M., O'Brien, S.C., Pan, C., Xiao, Z., Billups, W.E., Ciufolini, M.A., Hauge, R.H., Margrave, J.L., Wilson, L.J., Curl, R.F., Smalley, R.E., J. Phys. Chem., 94 8634, (1990).Google Scholar
d) Parker, D.H., Wurz, P., Chatterjee, K., Lykke, K.R., Hunt, J.E., Pellin, M.J., Hemminger, J.C., Gruen, D.M., Stock, L.M., J. Am. Chem. Soc, 113, 7499–7503, (1991).Google Scholar
[2] a) Haddon, R. C., Hebard, A.F., Rosseinsky, M.J., Murphy, D.W., Dulcos, K.B., Lyons, K.B., Miller, B., Rosamilia, J.M., Fleming, R.M., Kortan, A.R., Glarum, S.H., Makhija, A.V., Muller, A.J., Eick, R.H., Zahurak, S.M., Tycko, R., Dabbagh, G., Thiel, F.A., Nature, 350 320, (1990).Google Scholar
b) Hebard, A.F., Rosseinsky, M.J., Haddon, R.C., Murphy, D.W., Glarum, S.H., Palstra, T.T.M., Ramirez, A.P., Kortan, A.R., Nature, 350, 600, (1991).Google Scholar
[3] Hawkins, J. M., Lewis, T.A., Loren, S.D., Meyer, A., Heath, J.R., Shibato, Y., Saykally, R.J., J. Org. Chem., 55, 6250, (1990).Google Scholar
[4] Fagan, P. J., Calabrese, J.C., Malone, B., Science, 231, 1160, (1991).Google Scholar
[5] Wudl, F., Large Carbon Clusters, ACS Symposium, Atlanta, July 1991.Google Scholar
[6] Selig, H., Lifshitz, C., Peres, T., Fischer, J.E., Smith, A.B. III, McGhie, A.R., Romanow, W.J., McCauley, J.P. Jr, J. Am. Chem. Soc. Google Scholar
[7] We recently learned that polystyrene has been covalently modified with C60 at the University of Southern California: Olah, G. A., Bucsi, I., Lambert, C., Aniszfeld, R., Trivedi, N. J., Sensharma, D.K., Prakash, G. K. S., J. Am. Chem. Soc, in press.Google Scholar
[8] a) Krusic, P. J., Wasserman, E., Parkinson, B. A., Malone, B., Holler, E. R. Jr, Keizer, P. N., Morton, J. R., Preston, K. F., J. Am. Chem. Soc, 113, 6274, (1991).Google Scholar
b) Krusic, P. J., Wasserman, E., Keizer, P. N., Morton, J. R., Preston, K. F., Science, 254, 1183, (1991).Google Scholar
[9] Allemand, P. -M., Koch, A., Wudl, F., Rubin, Y., Diederich, F., Alvarez, M. M., Anz, S. J., Whetten, R. L., J. Am. Chem. Soc, 113, 1050, (1991).Google Scholar
[10] a) Szwarc, M., J. Polymer Sci., 6, 319, (1951).Google Scholar
b) Errebe, L. A., Landrum, B. F., J. Am. Chem. Soc, 82, 5218, (1960).Google Scholar
[11] The 13C NMR resonance of C60 has been reported at 142.7 ppm, Bausch, J. W., Prakash, G. K. S., Olah, G. A., Tse, D. S., Lorents, D. C., Bae, Y. K., Malhotra, R., J. Am. Chem. Soc., 113, 3205, (1991).Google Scholar
[12] Both Cross Polarization Magic Angle Spinning (CP MAS) and direct pulse MAS NMR spectroscopy were used to characterize poly-p-xylylene. Details of these studies will be published elsewhere. The poly-p-xylylene was prepared from paracyclophane using the same apparatus as with the co-polymerization of C60 and xylylene, save that the xylylene was allowed to polymerize on the quartz tube at room temperature.Google Scholar
[13] In interrupted decoupling experiments, delays of 60 and 90 μsec was inserted between cross polarization and acquisition. Because dipolar coupling depends on the inverse cube of the C-H distance, carbons with hydrogen substituents are typically more attenuated.Google Scholar
[14] α,α'-13C-labeled xylylene was prepared by the flash thermolysis of α, α'-13C-labeIed p- xylene, 99 atom%, at 1000 °C.Google Scholar
[15] Milliken, J., Keller, T. M., Baronavsky, A. P., McElvany, S. W., Callanhan, J. H., Nelson, H. H., Chem. Matet 3, 386, (1991).Google Scholar
[16] Joesten, B. L., J. Appl. Polym. Sci., 18, 439 (1974).Google Scholar
[17] Infrared analysis of the residue reveals loss of the majority of the absorption bands from the copolymer.Google Scholar
[18] Elemental analyses for carbon and hydrogen were carried out in duplicate on a Perkin- Elmer CHN Elemental Analyzer. The copolymer is relatively resistant to oxidation and care must be taken to insure that the sample is completely combusted.Google Scholar
[19] The xylylene:C60 ratio was calculated from the ratio of carbon to hydrogen with the assumption that all of the hydrogen in the material originated from xylylene monomers and that the contribution from terminal xylylene monomers was negligible.Google Scholar
[20] a) Infrared spectrum of the C60-p-xylylene copolymer (KBr): 3018, 2921, 2854, 1780, 1607, 1512, 1438, 1418, 1186, 1021, 820.4, 765.1, 727.8, 674.8, 543.2, 525.4 cm−1,Google Scholar
b) Joesten, B.L., Polymer Preprints 13, 1948, (1972).Google Scholar