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Fullerene derivative and methods for producing same

Foreign code F110003817
File No. E07902WO
Posted date Jul 5, 2011
Country United States of America
Application number 29400207
Gazette No. 20090118527
Gazette No. 7790913
Date of filing Mar 15, 2007
Gazette Date May 7, 2009
Gazette Date Sep 7, 2010
International application number JP2007055933
International publication number WO2007111226
Date of international filing Mar 15, 2007
Date of international publication Oct 4, 2007
Priority data
  • P2006-081836 (Mar 24, 2006) JP
  • 2007WO-JP55933 (Mar 15, 2007) WO
Title Fullerene derivative and methods for producing same
Abstract (US7790913)
The present invention provides a method for producing a fullerene derivative comprising reacting: a fullerene; an organometallic reagent (A) comprising B, Al, Zn, Sn, Pb, Te, Ti, Mn, Zr or Sm; and a copper compound (B).
Scope of claims [claim1]
1. A method for producing a fullerene derivative comprising reacting: a fullerene;
an organometallic reagent (A) comprising: a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryalkyl group or a substituted or unsubstituted aryl group; and B, Al, Zn, Sn, Pb, Te, Ti, Mn, Zr or Sm; and
a copper compound (B).
[claim2]
14. A fullerene derivative represented by the following formula (3):
wherein R5 is a hydrogen atom or a substituted or unsubstituted C1-C20 hydrocarbon group; and each R6 is independently a hydrogen atom or a substituted or unsubstituted C1-C20 hydrocarbon group.
[claim3]
17. A fullerene derivative represented by the following formula (4):
wherein each R6 is independently a hydrogen atom or a substituted or unsubstituted C1-C20 hydrocarbon group; M is a metallic atom; L is a ligand of M; and n is the number of Ls.
[claim4]
2. A method for producing a fullerene derivative comprising reacting: a fullerene;
an organometallic reagent (A) comprising: a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryalkyl group or a substituted or unsubstituted aryl group; and Al, Zn, Sn or Pb; and
a copper compound (B).
[claim5]
3. A method for producing a fullerene derivative comprising reacting: a C60 fullerene;
an organometallic reagent (A) comprising: an alkyl group which may have one or more substituents selected from the group consisting of an ester group, an amide group, a cyano group and a halogen atom, an alkenyl group which may have one or more substituents selected from the group consisting of an ester group, an amide group, a cyano group and a halogen atom, or an aryl group which may have one or more substituents selected from the group consisting of an ester group, an amide group, a cyano group and a halogen atom; and Zn; and
a monovalent or divalent copper compound (B).
[claim6]
4. The method for producing a fullerene derivative according to claim 1, wherein the fullerene derivative is represented by the following formula (1):
Cn(R4)m(R5)P (1)
wherein n is an even number of 60 or more; m is an integer from 3 to 10; p is 1 or 2; each R4 is independently a hydrogen atom, a substituted or unsubstituted C1-C20 hydrocarbon group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylthio group ( -- SY1: in the formula, Y1 is a substituted or unsubstituted C1-C20 alkyl group), a substituted or unsubstituted arylthio group ( -- SY2: in the formula, Y2 is a substituted or unsubstituted C6-C18 aryl group), a substituted or unsubstituted alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 is a substituted or unsubstituted C1-C20 alkyl group), or a substituted or unsubstituted arylsulfonyl group ( -- SO2Y4: in the formula, Y4 is a substituted or unsubstituted C6-C18 aryl group); and R5 is a hydrogen atom or a C1-C20 hydrocarbon group.
[claim7]
5. The method for producing a fullerene derivative according to claim 1, wherein the fullerene derivative is a fullerene derivative C60(R4)5R5 represented by the following formula (2):
wherein each R4 is independently a hydrogen atom, a substituted or unsubstituted C1-C20 hydrocarbon group, a substituted or unsubstituted C6-C20 alkoxy group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkylthio group ( -- SY1: in the formula, Y1 is a substituted or unsubstituted C1-C20 alkyl group), a substituted or unsubstituted arylthio group ( -- SY2: in the formula, Y2 is a substituted or unsubstituted C6-C18 aryl group), a substituted or unsubstituted alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 is a substituted or unsubstituted C1-C20 alkyl group), or a substituted or unsubstituted arylsulfonyl group ( -- SO2Y4: in the formula, Y4 is a substituted or unsubstituted C6-C18 aryl group); and R5 is a hydrogen atom or a C1-C20 hydrocarbon group.
[claim8]
6. The method for producing a fullerene derivative according to claim 4, wherein R4 has one or more substituents selected from the group consisting of an ester group, a carboxyl group, an amide group, an alkyne group, a trimethylsilyl group, a trimethylsilylethynyl group, an aryl group, an amino group, a phosphonyl group, a thio group, a carbonyl group, a nitro group, a sulfo group, an imino group, a halogeno group, and an alkoxy group.
[claim9]
7. The method for producing a fullerene derivative according to claim 4, wherein R4 has one or more substituents selected from the group consisting of an ester group, an amide group, an alkyne group, a trimethylsilyl group, a trimethylsilylethynyl group, and an aryl group.
[claim10]
8. The method for producing a fullerene derivative according to claim 4, wherein R5 is a hydrogen atom or a C1-C20 alkyl group.
[claim11]
9. The method for producing a fullerene derivative according to claim 4, wherein the fullerene derivative is represented by the following formula (3):
wherein R5 is a hydrogen atom or a substituted or unsubstituted C1-C20 hydrocarbon group; and each R6 is independently a hydrogen atom or a substituted or unsubstituted C1-C20 hydrocarbon group.
[claim12]
10. The method for producing a fullerene derivative according to claim 9, wherein R5 is a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group.
[claim13]
11. The method for producing a fullerene derivative according to claim 9, wherein R6 is a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, or a substituted or unsubstituted C2-C20 alkynyl group.
[claim14]
12. The method for producing a fullerene derivative according to claim 1, wherein an organic group included in the organometallic reagent (A) is a methyl group, an ethyl group, an isopropyl group, a butyl group or a phenyl group.
[claim15]
13. The method for producing a fullerene derivative according to claim 1 , wherein the copper compound (B) is CuBr.S(CH3)2.
[claim16]
15. The fullerene derivative according to claim 14, wherein R5 is a hydrogen atom or a substituted or unsubstituted C1-C20 alkyl group.
[claim17]
16. The fullerene derivative according to claim 14, wherein R6 is a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, or a substituted or unsubstituted C2-C20 alkynyl group.
[claim18]
18. The fullerene derivative according to claim 17, wherein R6 is a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, or a substituted or unsubstituted C2-C20 alkynyl group.
[claim19]
19. The fullerene derivative according to claim 17, wherein M is a transition metal.
[claim20]
20. The fullerene derivative according to claim 17, wherein M is a group 8-10 transition metal.
[claim21]
21. The fullerene derivative according to claim 17, wherein: M is Fe, Ru, or Os; n is an integer from 0 to 5; and L is a halogen atom, alkoxy group, alkyl group, alkyne group or cyclopentadienyl group.
  • Inventor, and Inventor/Applicant
  • NAKAMURA EIICHI
  • MATSUO YUTAKA
  • NAKAE TAKAHIRO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO NAKAMURA Functional Carbon Cluster AREA
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