Carbon Nanotube Chemistry
The organic chemistry of carbon nanotubes presents us with a new set of challenges, not the least of which is the complete insolubility of these materials. We are actively involved with a set of researchers, including Professors Selegue and Anthony, as well as Dr. Rodney Andrews at the Center for Applied Energy Research, who are developing new chemical processes for making nanotube-based composite materials. Chemical functionalization of nanotubes is essential for dispersion in a composite, as well as for covalent bonding with the matrix material itself.
We have been investigating both classical cylindrical multiwalled carbon nanotubes (MWNTs) as well as a type of nanotube that is composed of a series of stacked cups. This structure resembles bamboo, and it presents a very different surface to the surrounding medium. Cylindical MWNTs present basal plane graphite to the outside, while bamboo MWNTs present graphene edges. This results in a dramatic shift in reactivity, we are able to exploit these differences to producing some interesting changes in structure.
Our research is at the interface of molecular chemistry and materials chemistry, and we collaborate closely with chemical engineers at the Center for Applied Energy Research. Through this collaboration we are able to participate in projects where we tailor nanotubes for use in a variety of composite matrices.
- "7,8-Dichloromethanohomofullerene, an Unusual but Unexceptional Methanoannulene," Kiely, A. F.; Meier, M. S.; Patrick, B. O.; Selegue, J. P.; Brock, C. P. Helv. Chim. Acta 2003, 86, 1140-1151.
- “Monoalkylation of C60 and C70 with Zn and Active Alkyl Halides,” Wang, Z.; Meier, M. S.; J. Org. Chem. 2003, 68, 3043-3048.
- “Thermogravimetric Analysis of the Oxidation of Multi-Walled Carbon Nanotubes: Evidence for the Role of Defect Sites in Carbon Nanotube Chemistry,” Bom, D.; Andrews, R.; Jacques, D.; Anthony, J.; Chen, B.; Meier, M. S.; Selegue, J. P.Nanoletters, 2002, 2, 615-619.
- “A 13C INADEQUATE and HF-GIAO Study of C60H2 and C60H6. Identification of Ring Currents in a 1,2-Dihydrofullerene,” Meier, M. S.; Spielmann, H.P.; Haddon, R. C.; Bergosh, R. G.; J. Am. Chem. Soc. 2002, 124, 8090-8094.
- “Alkylation of Dihydrofullerenes,” Meier, M. S.; Bergosh, R. G.; Gallagher, M. E.; Spielmann, H. P.; Wang, Z. J. Org. Chem. 2002, 67, 5946-5952.
- “A Novel Synthesis of Branched High Molecular Weight (C40+) Long-Chain Alkanes,” Lehmler, H-J., Bergosh, R. G., Meier, M. S., Carlson, R. M. K., Bioscience, Biotechnology, and Biochemistry, 2002, 66, 523-531.
- "Chromatographic Purification and Properties of Soluble Single-Walled Carbon Nanotubes," Zhao, Z.; Hu, H.; Niyogi, S.; Itkis, M. E.; Hamon, M. A.; Bhowmik, P.; Meier, M. S.; Haddon, R. C. J. Am. Chem. Soc. 2001, 123, 11673-11677/LI>
- “Chromatographic Purification of Soluble Single Walled Carbon Nanotubes (s-SWNTs),” Niyogi, S.; Hamon, M. A.; Bhowmik, P.; Rozenzhak, S. M.; Itkis, M. E.; Meier, M. S.; Haddon, R. C. J. Am. Chem. Soc., 2001, 123, 733-734.
- The Synthesis and Characterization of Fullerene Hydrides,” Nossal, J.; Saini, R. K.; Billups, W. E.; Meier, M.; Euro. J. Chem. 2001, 4167-4180.
- “Preparation and Characterization of the Fullerene Diols 1,2-C60(OH)2, 1,2-C70(OH)2,and 5,6-C70(OH)2,” Meier, M. S.; Kiegiel, J. Org. Lett.2001, 3, 1717-1719.
- "Reactivity, Spectroscopy, and Structure of Reduced Fullerenes," Meier, M. S.; Spielmann, H. P.; Haddon, R. C.; Bergosh, R. C.; Gallagher, M. E.; Hamon, M. A.; Weedon, B. R. , Carbon, 2000, 38, 1535-1538.
- "Preparation and NMR Characterization of C70H10: Cutting a Fullerene J. Org. Chem., 2000, 65, 2755-2758.
- Wang, G.-W., Weedon, B. R., Meier, M. S., Saunders, M., Cross, R. A 3He NMR Study of 3He@C60H6 and 3He@C70H2-10, Org. Lett, 2000, 2, 2241-2243.
- Bachilo, S. M.; Benedetto, A. F.; Weisman, R. B.; Meier, M. S.; Wang, G.-W.; Weedon, B. R.; Selegue, J. P. "Photophysical Studies of C70-Benzyne Monoadducts: Strong Isomer Effects," Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials 2000, 281-288.
- Kiely, A.; Haddon, R. C.; Meier. M. S.; Selegue. J. P.; Brock, C. P.; Wang, G.-W.; Chen. Y. "The First Structurally Characterized Homofullerene (Fulleroid): 7,8-Dichloromethano-homofullerene," J. Am. Chem. Soc. 1999, 121, 7971-7972.
- Weedon, B. R.; Haddon, R. C.; Spielmann, H. P.; Meier, M. S. "Fulleroid Addition Regiochemistry Is Driven By p-Orbital Misalignment," J. Am. Chem. Soc.1999 121, 335-340.
- Spielmann, H. P.; Wang, G.-W., Meier, M. S.; Weedon, B. R. "Preparation of C70H2, C70H4 and C70H8: Three Independent Reduction Manifolds in the Zn(Cu) Reduction of C70," J. Org. Chem. 1998, 63, 9865-9871.
- "Benzyne Adds Across a Closed 5-6 Ring Fusion in C70 : Evidence for Bond Delocalization in Fullerenes," M. S. Meier, G. W. Wang, R. C. Haddon, C. P. Brock, M. A. Lloyd, J. P. Selegue, J. Am. Chem. Soc. 1998, 120, 2337-2342.
- R. G. Bergosh, J. A. Laske Cooke, M. S. Meier, H. P. Spielmann, B. R. Weedon, "Dissolving Metal Reductions of Fullerenes," J. Org. Chem. 62, 7667-7672 (1997).
- M. S. Meier, M. Poplawska, The Addition of Nitrile Oxides to C60," Tetrahedron 60, 5043-5052 (1996).
- M. S. Meier, B. R. Weedon, H. P. Spielmann, Synthesis and Isolation of One Isomer of C60H6," J. Am. Chem. Soc. 118, 11682-11683 (1996).
- M. S. Meier, D. J. Rice, "Linking Fullerene Units," R. S. Ruoff, K. M. Kadish, Eds., Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, Reno, NV (The Electrochemical Society, 1995).
- M. S. Meier, V. K. Vance, P. K. Corbin, M. Clayton, M. Mollman, M. Poplawska, "Synthesis of Hydrogenated Fullerenes by Zinc/Acid Reduction," Tetrahedron Lett. 35, 5789-5792 (1994).
- M. S. Meier, M. Poplawska, A. L. Compton, J. Shaw, J. P. Selegue, T. F. Guarr, "Preparation and Isolation of Three Isomeric C70 Isoxazolines: Strong Deshielding in the Polar Region of C70," J. Am. Chem. Soc. 116, 7044-7048 (1994).
- M. S. Meier, D. J. Rice, C. J. Thomas, V. Majidi, R. Pogue, M. Poplawska, "Fullerenes as Nanoscale Connectors," P. Bernier, et al., Eds., Science and Technology of Fullerene Materials, Boston, MA (Materials Research Society, 1994).
- T. F. Guarr, M. S. Meier, V. K. Vance and M. Clayton, "Electrochemistry of the C60H2 Fullerene," J. Am. Chem. Soc., 115, 9862-9863 (1993).
- M. S. Meier and M. Poplawska, "Addition of Nitrile Oxides to C60: Formation of Isoxazoline Derivatives of Fullerenes," J. Org. Chem., 58, 4524-4525 (1993).
- M. S. Meier, T. F. Guarr, J. P. Selegue and V. K. Vance, "Elevated Temperature Gel Permeation Chromatography and Electrochemical Behavior of the C84 Fullerene," J. Chem. Soc., Chem. Commun., 63-65 (1993).
- S. Ren, Y. Wang, A. M. Rao, M. S. Meier, J. P. Selegue and P. C. Eklund, "Dielectric Function of C70 Films," Appl. Phys. Lett., 61, 124-126 (1992).
- M. S. Meier and J. P. Selegue, "Efficient Preparative Separation of C60 and C70. Gel Permeation Chromatography of Fullerenes Using 100% Toluene as Mobile Phase," J. Org. Chem., 57, 1924-1926 (1992).