United States Patent | 5,338,529 |
Pirkle, et. al. | Aug. 16, 1994 |
Inventors: | Pirkle; William H. (Champaign, IL); Welch; Christopher J. (Northbrook, IL). |
Assignee: | Research Corporation Technologies, Inc. (Tucson, AZ). |
Appl. No.: | 874,791 |
Filed: | Apr. 27, 1992 |
Intl. Cl.: | C01B 31/00; |
U.S. Cl.: | 423/445.B; 423/461.; |
Field of Search: | 445 B;460;461;445;DIG. 39 |
Welch et al., "Progress in the Design of Selectors for Buckminsterfullerenes", Journ. of Chrom, 609 Sep. 18, 1992 pp. 89-101.
Ajie et al. "Characterization of the Soluble All Carbon Molecules C(60) and C(70) " Journ. Phys. Chem. 94, 1990 pp. 8630-8633.
Kikuchi et al., "Separation, Detection, and UV/Visible Absorption Spectra of Fullerenes; C(76), C(78) an C(84) ", Chem. Letters No. 9, Sep., 1991, pp. 1607-1610.
Dayan, et al. (1991) "Regulation of Molecular Conformation of Chiral Tripodal Structures by Ca(^2+) Binding", 113, American Chemical Society, 3431-3439.
Tor, et al. (1987) "A Trispeptide Circularly Organized Through Inter-Chain Hydrogen Bonds", J. Chem. Soc. Commun., 749-750.
Guggi, et al. (1976) "Neutraler Ionophor fur Flussigmembranelektroden mit hoher Selektivitat fur Natrium- gegenuber Kalium-Ionen" 59, Helvetica Chimica Acta, 2417-2420.
Tor, et al. (1987) "Biomimetic Ferric Ion Carriers. A Chiral Analogue of Enterobactin", 109, J. Am. Chem. Soc., 6517-6518.
Roush, et al. (1985) "Cascade Molecules: A New Approach to Micelles". A [27]-Arborol, 50, J. Org. Chem., 2003-2004.
Dunn, et al. (1990) "Versatile Methods for the Synthesis of Differentially Functionalized Pentaerythritol Amine Derivatives", 55, J. Org. Chem., 6368-6373.
Fleischer, et al. (1971) "Conversion of Aliphatic and Alicyclic Polyalcohols to the Corresponding Primary Polyamines", 36, J. Org. Chem., 3042-3044.
Kratschmer, et al. (1990) "Solid C(60) : A New Form of Carbon", 347, Nature, 354-358.
Taylor, et al. (1990) "Isolation, Separation and Characterization of the Fullerenes C(60) and C(70) : The Third Form of Carbon", J. Chem. Soc. Commun., 1423-1425.
Howard, et al. (1991) "Fullerenes C(60) and C(70) in Flames", 352, Nature, 139-141.
Kroto, et al. (1991) "C(60) : Buckminsterfullerene" 91, Chem. Rev., 1213-1235.
Hawkins, et al. (1990) "Organic Chemistry of C(60) (Buckminsterfullerene): Chromatography and Osmylation", 55, J. Org. Chem., 6250-6252.
Cox, et al. (1991) "Characterization of C(60) and C(70) Clusters", 113, J. Am. Chem. Soc., 2940-2944.
Pirkle, et al. (1991) "An Unusual Effect of Temperature on the Chromatographic Behavior of Buckminsterfullerene", 56, J. Org. Chem., 6973-6974.
Johnson, et al. (1990) "C(60) has Icosahedral Symmetry", 112, J. Am. Chem. Soc., 8984-8985.
Lochmuller "Chemically-Bonded, Charge Transfer Acceptors for High-Performance Liquid Chromatography", Midland Macromolecular Symposium on Silylated Surfaces for High Performance Liquid Chromatography, 231 (1980).
Nondek (1986) "Liquid Chromatography on Chemically Bonded Electron Donors and Acceptors", 373, Journal of Chromatography, 61-80.
Cram (1986) "Preorganization-From Solvents to Spherands", 25, Angw. Chem. Int. Ed. Engl., 1039-1057.
Weibull, et al. (1962) "The Synthesis of Some 1,1,1-Trishydroxymethylalkanes", 16, Acta Chem. Scand., 1062.
Pirkle, et al. (1991) "A Convenient Void Volume Marker for Several Chiral HPLC Columns", 14, Journal of Liquid Chromatography, 1-8.
Atwood, et al. (1991) "X-ray Diffraction Evidence for Aromatic .pi. Hydrogen Bonding to Water", 349, Nature, 683-684.
Krusic, et al. (1991) "Radical Reactions of C(60) ", 254, Science, 1183-1185.
Suzuki, et al. (1991) "Systematic Inflation of Buckminsterfullerene C(60:) Synthesis of Diphenyl Fulleroids C(61) to C(66) ", 254, Science, 1186-1188.
Baum (1990) "Simple Synthesis of C(60) Molecule Triggers Intense Research Effort", C & EN, 22-25.
Maggs (1969) "The Role of Temperature in Liquid-Solid Chromatography: Some Practical Considerations", 7, Journal of Chromatographic Science, 145-151.
Chang (1953) "Effect of Temperature on Movement of a Chromatographic Zone", 25, Analytical Chemistry, 1235-1237.
Jinno, et al. "Liquid Chromatographic Separation of All-Carbon Molecules C(60) and C(70) with Multi-Legged Phenyl Group Bonded Silica Phases", 594, Journal of Chromatography, 105-109, Mar. 6, 1992.
Carbon clusters, such as C(60) and C(70) fullerenes are separated by means of a recognition selector having the formula: ##STR1## wherein R(1) is ##STR2## wherein R(2) is O, S or NR(12) wherein R(12) is independently hydrogen or P.dbd.O with the proviso that when R(12) is P.dbd.O, then only one such group is present and all R(2) 's are additionally bonded to R(12),
R(4) is independently O, S or NH,
R(3) and R(5) are each independently hydrogen or lower alkyl,
n and o are each independently zero, 1, 2 or 3,
p, q, r, s and t are each independently zero or 1,
Ar is a monocyclic or ortho-fused polycyclic aromatic moiety having up to 10 carbon atoms, either of which may be unsubstituted or substituted with one or more lower alkyl, NO(2), N(R(6))(3)(^+), CN, COOR(7), SO(3) H, COR(8) and OR(9) wherein R(6), R(7), R(8) and R(9) are each independently hydrogen or lower alkyl;
W is H or CH.dbd.CH(2) ; and
m is 1 to 10.
The invention described herein was made with Government support under Grant NSF CHE 87-14950 awarded by The National Science Foundation. The Government has certain rights in the invention.