Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1993-11-24
1995-01-31
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
556432, 556435, 556452, 556453, 556457, 556465, 556479, 556482, 556489, C07F 708, C07F 718
Patent
active
053860489
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Technical Field
This invention relates generally to silicon-substituted fullerene compounds and methods of making them.
2. Background Art
Fullerenes are a recently discovered form of pure solid carbon. They are cage-like hollow structures comprised of hexagon and pentagon rings fused together to form ball shaped hollow molecules which resemble geodesic domes. Fullerenes may range from 32 carbons up to many hundreds of carbon atoms. A fullerene molecule containing 60 carbons (C.sub.60) is the archetype, and is known as Buckminsterfullerene. For a general discussion of fullerenes, see R. Curl, et al., Scientific American, 54-63 (October 1991). The disclosure of this articles, and of all other articles referred to herein, are incorporated by reference as if fully set forth herein.
Fullerenes have been synthesized by decomposing graphite rods in the presence of helium. Graphite rod decomposition may be accomplished by electric arc, as discussed in A. Koch, et al., 56 Journal of Organic Chemistry, 4543-4545 (1991)(C.sub.60 ; C.sub.70), or by plasma discharge as discussed in D. Parker; et al., 113 Journal American Chemical Society, 7499-7503 (1991)(C.sub.60 -C.sub.266).
Researchers have identified many interesting uses of fullerenes over the past few years. For example, fullerenes show promise for use in diamond films, nonlinear optical and superconducting materials, semiconductors, and photo-conductors. Because pure fullerenes form discreet crystals, more processable forms of fullerenes are needed to more fully exploit their unique properties.
A few polymers of fullerenes have been synthesized to help meet this need. In this regard, D. Loy, et al. synthesized a C.sub.60 -p-xylyene copolymer. See, 114 Journal American Chemical Society, 3977-3978 (1992). Another example is a palladium polymer of a Buckminsterfullerene synthesized by H. Nagashima, et al., Journal of the Chemical Society, "Chemical Communications", 377-379 (1992). Other examples are the synthesis by S. Shi, et al. of a polyester and polyurethane of diphenyl C.sub.61. (See, 114 Journal American Chemical Society, 10656-10657 (1992)) and a polymer-substituted fullerene shown in E. Samulski, et al., 4 Chemical Materials, 1153-1157 (1992).
A drawback of some of the foregoing substituted fullerenes is that they employ expensive reagents, like palladium and xylylene. Further, some are made from reagents which have toxic side effects. Accordingly, there is a need for an inexpensive and non-toxic polymeric substituted fullerene.
Disclosure Of Invention
One aspect of the invention provides a compound having the moiety C.sub.n --A--C.sub.m where C.sub.n and C.sub.m are ball-shaped, n and m are numbers above 59 and below 267, and A is a linker in which Si on the linker is directly attached to both C.sub.n and C.sub.m. The linker preferably contains the moiety: ##STR1## where R.sub.1 through R.sub.4 4 are selected from the group consisting of hydrogen, halide, aryl, alkyl, silyl, siloxy, and alkoxy, and where B is selected from the group consisting of nothing, oxygen, alkyl and aryl. Preferably, the alkyl and alkoxy groups contain from one to six carbons. The aryl preferably contains a phenyl moiety. This version of the invention is the polymeric version.
The preferred method for making these compounds is to conduct a hydrosilylation reaction between C.sub.n, C.sub.m, and at least two linker segments, wherein both linker segments have an SiH terminus.
Another version of the invention provides a compound having the moiety: ##STR2## wherein C.sub.n is ball-shaped, n is a number above 59 and below 267, D is linked via Si bridges to at least two points on the C.sub.n, and D contains a moiety that is selected from the group consisting of silane, siloxane, polysilane, and polysiloxane. In this aspect of the invention, a fullerene is "shrink-wrapped" by functional silicon moieties to form a somewhat rubbery substance.
The preferred method for making these compounds is to conduct a hydrosilylation reaction between C.sub.n and at least
REFERENCES:
J. Speier, "Homogeneous Catalysis Hydrosilation by Transition Metals", 17 Advances in Organometallic Chemistry 407-477 (1979.
D. Parker, et al., High-Yield Synthesis, Separation, and Mass-Spectrometric Characterization of Fullerenes C.sub.60 to C.sub.266, 113 J. Am. Chem. Soc. 7499-7503 (1991).
A. Koch, et al., Preparation of Fullerenes with a Simple Benchtop Reactor, 56 J. Org. Chem. 4543-4545 (1991).
Curl, et al., Fullerenes, Scientific American 54-63 (Oct. 1991).
P. Bhyrappa et al., Improved Chromatographic Separation and Purification of C.sub.60 and C.sub.70 Fullerenes, J. Chem. Soc. Chem. Comm. 936-937 (1992).
Chemical Abstracts, Is it possible to recognize organic molecules by controlling silica gel surface?, 116:186757u (1992).
Bausch et al., Diamagnetic Polyanions of the C.sub.60 and C.sub.70 Fullerenes: Preparation, .sup.13 C and .sup.7 Li NMR Spectroscopic Observation, and Alkylation with Methyl Iodite to Polymethylated Fullerenes, 113 J. Am. Chem. Soc. 3205-3206 (1991).
S. Shi, et al., A Polyester and Polyurethane of Diphenyl C.sub.61 : Retention of Fulleroid Properties in a Polymer, 114 J. Am. Chem. Soc. 10656-10657 (1992).
E. Samulski, et al., Flagellenes: Nanophase-Separated, Polymer-Substituted Fullerenes, 4 Chem. Mater. 1153-1157 (1992).
H. Nagashima, et al., C.sub.60 Pd.sub.n : The First Organometallic Polymer of Buckministerfullerene, J. Chem. Soc., Chem. Commun. 377-379 (1992).
D. Loy, et al., Synthesis of a C.sub.60 -p-Xylylene Copolymer, 114 Amer. Chem. Soc. 3977-3978 (1992).
I. Ojima, "The Hydrosilylation Reaction", The Chemistry of Organic Silicon Compounds, Edited by S. Patai, et al., 1479-1499 (1989).
Oka Kunio
West Robert C.
Shaver Paul F.
Wisconsin Alumni Research Foundation
LandOfFree
Hydrosilylation of fullerenes does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Hydrosilylation of fullerenes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hydrosilylation of fullerenes will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1103519