Fullerene derivatives and their metal complexes

Details Fullerene derivatives and their metal complexes Fullerene derivatives and their metal complexes

2007-04-10

2007-04-10

Wilson, James O. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

C556S465000, C260S66500B, C585S026000

Reexamination Certificate

active

11149196

ABSTRACT:
A metal complex contains at least one ligand, each having the form of a molecule of a fullerene derivative or an anion of the fullerene derivative, where the fullerene derivative, with a solubility in n-hexane of not lower that 0.1 mg/ml at 250° C., includes a fullerene skeleton and three or more organic groups attached to the fullerene skeleton, where each of the organic groups is represented by the general formula (III):in-line-formulae description="In-line Formulae" end="lead"?—CH2—X(R2)(R3)(R4)   (III)in-line-formulae description="In-line Formulae" end="tail"?where X represents an element belonging to the group 14 in the periodic table; and R2, R3and R4may be the same or different and each represents a hydrogen atom, hydrocarbon group, alkoxy group or amino group.

REFERENCES:
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M. Sawamura, et al., “Synthesis of π-Idenyl-type Fullerene Ligand and Its Metal Complexes via Quantitative Trisarylation of C70”, J. Am. Chem. Soc. vol. 120, (1998, pp. 8285-8286).
H. Nagashima, et al., “Silylmethylations of C60 with Grignard Reagents: Selective Synthesis of HC60CH60CH2SiMe2Y and C60(CH2SiMe2Y)2 with Selection of Solvents”, J. Org. Chem. vol. 59, (1994, pp. 1246-1248).
Gendai Kagaku (Modern Chemistry), Jun. 2000, p. 46.
N. Martin, et al., “C60-Based Electroactive Organofullerenes”, Chem. Rev., v. 98 (1998), pp. 2527-2547.
M. Sawamura, et al., “The First Pentahaptofullerene Metal Complexes”, J. Am. Chem. Soc. v. 118 (1996), pp. 12850-12851.
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H. Nagashima, et al., Chemistry Letters., No. 6, XP-009018165, pp. 469-470, “Efficient Photooxygenation of Olefins by a C60Derivative Bearing an Organofluorine Tail”, (1999).
H. Nagashima, et al. Tetrahedron, v. 52, No. 14 XP-004104260, pp. 5053-5064, “Electronic Structures and Redox Properties of Silymethylated C60” (1996).
H. Nagashima, et al., J. Org. Chem., v. 60, No. 16, XP-002258204, pp. 4966-4967, “Chlorosilanes and Silyl Triflates Containing C60as a Partial Structure. A Versatile Synthetic Entry Linking the C60Moieties with Alcohols, Phenols, and Silica”, Aug. 11, 1995.
K. Fujiwara, et al., Tetrahedron, v. 54, No. 10, XP-004109543, pp. 2049-2058, “Synthesis of a Propargyl Alcohol Having a C60Cage, its Transformation into C60Derivatives with Polar Functional Groups, and the Solubility Measurements”, Mar. 5, 1998.
J. Bourgeois, et al., Helvetica Chimica Acta, v. 84, XP-002258206, pp. 1207-1226 “Hexakis-Adducts of [60] Fullerene With Different Addition Patterns: Templated Synthesis, Physical Properties, and Chemical Reactivity”, May 16, 2001.
S. M. Draper, et al., J. Organometallic Chem., v. 589, XP-002258207, pp. 157-167, “Novel Acetylene-Linked Di-Cobalt And Tetra-Cobalt Carbonyl Clusters”, Nov. 5, 1999.
J. Nierengarten, et al., Helvetica Chimica Acta, v. 80, No. 1, XP-009018170, pp. 293-316, “25. Methanofullerene Molecular Scaffolding: Towards C60-Substituted Poly(triacetylenes) And Expanded Radialenes, Preparation of a C60—C70Hybrid Derivative, and A Novel Macrocyclization Reaction”, (1997).
P. Timmermann, et al., Helvetica Chimica Acta, v. 79, XP-009018169, pp. 6-20, “2. Fullerene-Acetylene Molecular Scaffolding:Chemistry of 2-Functionalized 1-Ethynylated C60Oxidative Homocoupling, Hexakis-Adduct Formation, and Attempted Synthesis of C2-124”, (1996).
M. Sawamura, et al., “Stepwise Synthesis of Fullerene Cyclopentadienide R5C60- and Indenide R3C60-. An Approach to Fully Unsymmetrically Substituted Derivatives”, Org. Letters, v. 2, No. 13, pp. 1919-1921, Apr. 27, 2000.
Nagashima, et al., “Silylmethylations of C60, with Grignard Reagents: Selective Synthesis of HC60CH2SiMe2Y and C60(CH2SiMe2Y)2with Selection of Solvents”, J. Org. Chem., v.59 (1994) pp. 1246-1248.
E. Allard, et al., “Chemical Generation and Reactivity of C602-. High-yield and Regioselective Alkylation of [60, lη] Fullerene”, Tetrahedron Letters, v. 40 (1999), pp. 7223-7226.
M. Sawamura, et al., “Pentaorgano[60]fullerene R5C60-. A Water Soluble Hydrocarbon Anion”, Chem. Letters, (2000) pp. 1098-1099.
M. Sawamura, et al., Synthesis of π-Idenyl-type Fullerene Ligand and Its Metal Complexes via Quantitative Trisarylation of C70′-, J. Am. Chem. Soc. v. 120, (1998) pp. 8285-8286.

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