System and method for manipulating nanotubes

• US 7,344,691 B2
• Filed: 12/10/2003
• Issued: 03/18/2008
• Est. Priority Date: 05/17/2001
• Status: Expired due to Term

• Current Assignee: Evermore Applied Materials Corp.
• Original Assignee: Zyvex Performance Materials, LLC
• Inventors: Dyer, Mark J., Chen, Jian
• Primary Examiner(s): Langel; Wayne A.
• Assistant Examiner(s): Fiorito; James
• Application Number:
  US10/732,490
• Publication Number:
  US 20040120879A1
• Time in Patent Office: 1,560 Days
• Field of Search: 423/447.2, 423/67, 423/56, 423/460, 977/750, 977/752, 977/847, 502/24, 502/26
• US Class Current: 423/447.2
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 40/00 Manufacture or treatment of nanostructures
• CPC Class Codes: C01B 2202/34 Length
• CPC Class Codes: C01B 32/176 Cutting
• CPC Class Codes: C01P 2004/04 obtained by TEM, STEM, STM or AFM
• CPC Class Codes: C01P 2004/13 Nanotubes
• CPC Class Codes: C01P 2004/64 Nanometer sized, i.e. from 1-100 nanometer
• CPC Class Codes: C09C 1/48 Carbon black
• CPC Class Codes: C09C 1/56 Treatment of carbon black ; Purification
• CPC Class Codes: D01F 9/12 Carbon filaments; Apparatus specially adapted for the manufacture thereof
• CPC Class Codes: Y10S 977/742 Carbon nanotubes, CNTs
• CPC Class Codes: Y10S 977/75 Single-walled
• CPC Class Codes: Y10S 977/752 Multi-walled
• CPC Class Codes: Y10S 977/842 for carbon nanotubes or fullerenes
• CPC Class Codes: Y10S 977/847 Surface modifications, e.g. functionalization, coating
• CPC Class Codes: Y10S 977/888 Shaping or removal of materials, e.g. etching

Abstract

A system and method for manipulation of nanotubes using an organic material that is presented to the nanotubes. Exemplary types of manipulation include cutting nanotubes into shortened nanotubes, dispersing nanotubes, enabling dissolution of nanotubes, and noncovalently functionalizing nanotubes. The organic material used in manipulating nanotubes preferably comprises a solid organic material, soluble organic material, and/or an organic material that acts as a dispersing reagent for dispersing nanotubes. In a preferred embodiment, the organic material used for manipulating nanotubes comprises cyclodextrin.

Claims

1. A method for manipulating single-walled carbon nanotubes comprising:

presenting a solid organic material to a plurality of single-walled nanotubes; and

using said solid organic material to manipulate said plurality of nanotubes, wherein said plurality of nanotubes are manipulated by at least one of;

(a) dispersing at least a portion of said plurality of nanotubes;

(b) dissolving at least a portion of said plurality of nanotubes in a solvent; and

(c) functionalizing at least a portion of said plurality of nanotubes.

2. The method of claim 1 wherein said solid organic material comprises a solid-state nanotube dispersing reagent, and said plurality of nanotubes are manipulated by dispersing at least a portion of said plurality of nanotubes with said dispersing reagent.

3. The method of claim 2 wherein said solid-state nanotube dispersing reagent comprises cyclodextrin.

4. The method of claim 3 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

5. The method of claim 2 wherein said solid-state nanotube dispersing reagent comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides, cyclic oligosaccharides, linear oligosaccharides, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

6. The method of claim 5 wherein said plurality of nanotubes are produced by a gas-phase catalytic reaction process.

7. The method of claim 5 wherein said plurality of nanotubes are produced by an electric arc process.

8. The method of claim 5 wherein said plurality of nanotubes are produced by a laser vaporization process.

9. The method of claim 1 further comprising grinding at least a portion of said plurality of nanotubes to cut said at least a portion of said plurality of nanotubes.

10. The method of claim 1 wherein said solid organic material is soluble in at least one member selected from the group consisting of an organic solvent and an inorganic solvent.

11. The method of claim 1 wherein said solid organic material comprises a nanotube-dispersing reagent, and wherein said nanotube-dispersing reagent is presented to said plurality of nanotubes in at least one solvent, and said plurality of nanotubes are manipulated by dissolving at least a portion of said plurality of nanotubes.

12. The method of claim 11 wherein said nanotube-dispersing reagent comprises cyclodextrin.

13. The method of claim 12 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

14. The method of claim 11 wherein said nanotube-dispersing reagent comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides, cyclic oligosaccharides, linear oligosaccharides, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

15. The method of claim 1 wherein said at least one nanotube has a diameter of at least 0.4 nm.

16. The method of claim 11 wherein said at least one solvent comprises an organic solvent.

17. The method of claim 16 wherein said organic solvent comprises at least one solvent selected from the group consisting of:

acetic acid;

acetone;

acetonitrile;

aniline;

benzene;

benzonitrile;

benzyl alcohol;

bromobenzene;

bromoform;

1-butanol;

2-butanol;

carbon disulfide;

carbon tetrachloride;

chlorobenzene;

chloroform;

cyclohexane;

cyclohexanol;

decalin;

dibromethane;

diethylene glycol;

diethylene glycol ethers;

diethyl ether;

diglyme;

dimethoxymethane;

N,N-dimethylformamide;

ethanol;

ethylamine;

ethylbenzene;

ethylene glycol ethers;

ethylene glycol;

ethylene oxide;

formaldehyde;

formic acid;

glycerol;

heptane;

hexane;

iodobenzene;

mesitylene;

methanol;

methoxybenzene;

methylamine;

methylene bromide;

methylene chloride;

methylpyridine;

morpholine;

naphthalene;

nitrobenzene;

nitromethane;

octane;

pentane;

pentyl alcohol;

phenol;

1-propanol;

2-propanol;

pyridine;

pyrrole;

pyrrolidine;

quinoline;

1,1,2,2-tetrachloroethane;

tetrachloroethylene;

tetrahydrofuran;

tetrahydropyran;

tetralin;

tetramethylethylenediamine;

thiophene;

toluene;

1,2,4-trichlorobenzene;

1,1,1-trichloroethane;

1,1,2-trichloroethane;

trichloroethylene;

triethylamine;

triethylene glycol dimethyl ether;

1,3,5-trimethylbenzene;

m-xylene;

o-xylene;

p-xylene;

1,2-dichlorobenzene;

1,3-dichlorobenzene; and

1,4-dichlorobenzene.

18. The method of claim 11 wherein said at least one solvent comprises an inorganic solvent.

19. The method of claim 18 wherein said inorganic solvent comprises water.

20. The method of claim 1 wherein said plurality of nanotubes are manipulated by selectively noncovalently functionalizing at least one of said plurality of nanotubes, based at least in part on a diameter of said at least one plurality of nanotubes.

21. The method of claim 20 wherein said noncovalently functionalizing comprises said organic material encaging said at least one of said plurality of nanotubes.

22. The method of claim 21 further comprising separating said noncovalently functionalized nanotubes based on diameter size of said organic material.

23. The method of claim 20 wherein said noncovalently functionalizing comprises forming at least one rotaxane complex.

24. The method of claim 20 wherein said noncovalently functionalizing enables dissolution of said at least one of said plurality of nanotubes in at least one solvent.

25. The method of claim 24 wherein said at least one solvent comprises an organic solvent selected from the group consisting of:

acetic acid;

acetone;

acetonitrile;

aniline;

benzene;

benzonitrile;

benzyl alcohol;

bromobenzene;

bromoform;

1-butanol;

2-butanol;

carbon disulfide;

carbon tetrachloride;

chlorobenzene;

chloroform;

cyclohexane;

cyclohexanol;

decalin;

dibromethane;

diethylene glycol;

diethylene glycol ethers;

diethyl ether;

diglyme;

dimethoxymethane;

N,N-dimethylformamide;

ethanol;

ethylamine;

ethylbenzene;

ethylene glycol ethers;

ethylene glycol;

ethylene oxide;

formaldehyde;

formic acid;

glycerol;

heptane;

hexane;

iodobenzene;

mesitylene;

methanol;

methoxybenzene;

methylamine;

methylene bromide;

methylene chloride;

methylpyridine;

morpholine;

naphthalene;

nitrobenzene;

nitromethane;

octane;

pentane;

pentyl alcohol;

phenol;

1-propanol;

2-propanol;

pyridine;

pyrrole;

pyrrolidine;

quinoline;

1,1,2,2-tetrachloroethane;

tetrachloroethylene;

tetrahydrofuran;

tetrahydropyran;

tetralin;

tetramethylethylenediamine;

thiophene;

toluene;

1,2,4-trichlorobenzene;

1,1,1-trichloroethane;

1,1,2-trichloroethane;

trichloroethylene;

triethylamine;

triethylene glycol dimethyl ether;

1,3,5-trimethylbenzene;

m-xylene;

o-xylene;

p-xylene;

1,2-dichlorobenzene;

1,3-dichlorobenzene; and

1,4-dichlorobenzene.

26. The method of claim 24 wherein said at least one solvent comprises an inorganic solvent.

27. The method of claim 20 wherein said organic material comprises cyclodextrin.

28. The method of claim 27 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

29. The method of claim 20 wherein said organic material comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides, cyclic oligosaccharides, linear oligosaccharides, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

30. The method of claim 20 wherein said organic material comprises at least one macrocyclic compound.

31. The method of claim 30 wherein said at least one macrocyclic compound contains at least one member selected from the group consisting of:

at least one glucopyranose unit, and at least one monosaccharide unit.

32. The method of claim 20 wherein said plurality of nanotubes include nanotubes that have diameters of at least 0.4 nm.

33. A method for manipulating single-walled carbon nanotubes comprising:

dispersing at least a portion of a plurality of single-walled carbon nanotubes with a solid organic material.

34. The method of claim 33 wherein said solid organic material comprises cyclodextrin.

35. The method of claim 34 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

36. The method of claim 33 wherein said solid organic material comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides, cyclic oligosaccharides, linear oligosaccharides, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

37. The method of claim 33 further comprising grinding at least a portion of said plurality of nanotubes to cut said at least a portion of said plurality of nanotubes.

38. A method for manipulating single-walled carbon nanotubes comprising:

mixing at least one solvent, a soluble organic material, and a plurality of single-walled carbon nanotubes; and

dissolving at least a portion of said plurality of nanotubes.

39. The method of claim 38 wherein said solid organic material comprises cyclodextrin.

40. The method of claim 39 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

41. The method of claim 38 wherein said solid organic material comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides, cyclic oligosaccharides, linear oligosaccharidcs, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

42. The method of claim 38 wherein said at least one solvent comprises an organic solvent.

43. The method of claim 42 wherein said organic solvent comprises at least one solvent selected from the group consisting of:

acetic acid;

acetone;

acetonitrile;

aniline;

benzene;

benzonitrile;

benzyl alcohol;

bromobenzene;

bromoform;

1-butanol;

2-butanol;

carbon disulfide;

carbon tetrachloride;

chlorobenzene;

chloroform;

cyclohexane;

cyclohexanol;

decalin;

dibromethane;

diethylene glycol;

diethylene glycol ethers;

diethyl ether;

diglyme;

dimethoxymethane;

N,N-dimethylformamide;

ethanol;

ethylamine;

ethylbenzene;

ethylene glycol ethers;

ethylene glycol;

ethylene oxide;

formaldehyde;

formic acid;

glycerol;

heptane;

hexane;

iodobenzene;

mesitylene;

methanol;

methoxybenzene;

methylamine;

methylene bromide;

methylene chloride;

methylpyridine;

morpholine;

naphthalcne;

nitrobenzene;

nitromethane;

octane;

pentane;

pentyl alcohol;

phenol;

1-propanol;

2-propanol;

pyridine;

pyrrole;

pyrrolidine;

quinoline;

1,1,2,2-tetrachloroethane;

tetrachloroethylene;

tetrahydrofuran;

tetrahydropyran;

tetralin;

tetramethylethylenediamine;

thiophene;

toluene;

1,2,4-trichlorobenzene;

1,1,1-trichloroethane;

1,1,2-trichloroethane;

trichloroethylene;

triethylamine;

triethylene glycol dimethyl ether;

1,3,5-trimethylbenzene;

m-xylene;

o-xylene;

p-xylene;

1,2-dichlorobenzene;

1,3-dichlorobenzene; and

1,4-dichlorobenzene.

44. The method of claim 38 wherein said at least one solvent comprises an inorganic solvent.

45. The method of claim 44 wherein said inorganic solvent comprises water.

46. A method for manipulating single-walled carbon nanotubes comprising:

selectively noncovalently functionalizing at least a portion of a plurality of single-walled carbon nanotubes with a solid organic material.

47. The method of claim 46 wherein said selective noncovalent functionalization is based at least in part on a diameter of said at least a portion of said plurality of nanotubes.

48. The method of claim 46 wherein said selective noncovalent functionalization comprises said solid organic material engaging at least one of said portion of said plurality of nanotubes.

49. The method of claim 48 further comprising separating said noncovalently functionalized nanotubes based on diameter size of said solid organic material.

50. The method of claim 46 wherein said selective noncovalent functionalization comprises forming at least one rotaxane complex.

51. The method of claim 46 wherein said selective noncovalent functionalization enables dissolution of said at least a portion of said plurality of nanotubes in at least one solvent.

52. The method of claim 51 wherein said at least one solvent comprises an organic solvent selected from the group consisting of:

acetic acid;

acetone;

acetonitrile;

aniline;

benzene;

benzonitrile;

benzyl alcohol;

bromobenzene;

bromoform;

1-butanol;

2-butanol;

carbon disulfide;

carbon tetrachloride;

chlorobenzene;

chloroform;

cyclohexane;

cyclohexanol;

decalin;

dibromethane;

diethylene glycol;

diethylene glycol ethers;

diethyl ether;

diglyme;

dimethoxymethane;

N,N-dimethylformamide;

ethanol;

ethylamine;

ethylbenzene;

ethylene glycol ethers;

ethylene glycol;

ethylene oxide;

formaldehyde;

formic acid;

glycerol;

heptane;

hexane;

iodobenzene;

mesitylene;

methanol;

methoxybenzene;

methylamine;

methylene bromide;

methylene chloride;

methylpyridine;

morpholine;

naphthalene;

nitrobenzene;

nitromethane;

octane;

pentane;

pentyl alcohol;

phenol;

1-propanol;

2-propanol;

pyridine;

pyrrole;

pyrrolidine;

quinoline;

1,1,2,2-tetrachloroethane;

tetrachloroethylene;

tetrahydrofuran;

tetrahydropyran;

tetralin;

tetramethylethylenediamine;

thiophene;

toluene;

1,2,4-trichlorobenzene;

1,1,1-trichloroethane;

1,1,2-trichloroethane;

trichloroethylene;

triethylamine;

triethylene glycol dimethyl ether;

1,3,5-trimethylbenzene;

m-xylene;

o-xylene;

p-xylene;

1,2-dichlorobenzene;

1,3-dichlorobenzene; and

1,4-dichlorobenzene.

53. The method of claim 51 wherein said at least one solvent comprises an inorganic solvent.

54. The method of claim 46 wherein said solid organic material comprises cyclodextrin.

55. The method of claim 54 wherein said cyclodextrin comprises at least one member selected from the group consisting of:

γ

-cyclodextrin, α

-cyclodextrin, β

-cyclodextrin, δ

-cyclodextrin, ε

-cyclodextrin, and derivatives thereof.

56. The method of claim 46 wherein said solid organic material comprises at least one member selected from the group consisting of:

glucopyranoses, monosaccharides;

cyclic oligosaccharides, linear oligosaccharides, branched oligosaccharides, cyclic polysaccharides, linear polysaccharides, branched polysaccharides, and derivatives thereof.

57. The method of claim 46 wherein said solid organic material comprises at least one macrocyclic compound.

58. The method of claim 57 wherein said at least one macrocyclic compound contains at least one member selected from the group consisting of:

at least one glucopyranose unit, and at least one monosaccharide unit.

59. The method of claim 46 wherein said plurality of nanotubes include nanotubes that have diameters of at least 0.4 nm.