WO2005049488A2 - Traitement thermique de nanotubes de carbone fonctionnalises en solution pour effectuer leur defonctionnalisation - Google Patents

Traitement thermique de nanotubes de carbone fonctionnalises en solution pour effectuer leur defonctionnalisation Download PDF

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WO2005049488A2
WO2005049488A2 PCT/US2004/035894 US2004035894W WO2005049488A2 WO 2005049488 A2 WO2005049488 A2 WO 2005049488A2 US 2004035894 W US2004035894 W US 2004035894W WO 2005049488 A2 WO2005049488 A2 WO 2005049488A2
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carbon nanotubes
defunctionalized
functionalized
cnts
defunctionalization
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PCT/US2004/035894
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English (en)
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WO2005049488A3 (fr
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James M. Tour
Christopher A. Dyke
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William Marsh Rice University
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Publication of WO2005049488A3 publication Critical patent/WO2005049488A3/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/158—Carbon nanotubes
    • C01B32/168—After-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/02—Single-walled nanotubes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/04—Nanotubes with a specific amount of walls
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/06—Multi-walled nanotubes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/20—Nanotubes characterized by their properties
    • C01B2202/22—Electronic properties

Definitions

  • the present invention relates generally to carbon nanotube materials. More specifically, the invention relates to methods of defunctionalizing previously functionalized carbon nanotubes.
  • Carbon nanotubes comprising multiple concentric shells and termed multi-wall carbon nanotubes (MWNTs), were discovered by lijima in 1991 [lijima, Nature 1991, 354, 56-58].
  • single-wall carbon nanotubes comprising single graphene sheets rolled up on themselves to form cylindrical tubes with nanoscale diameters, were synthesized in an arc- discharge process using carbon electrodes doped with transition metals [lijima et ai, Nature 1993, 363, 603-605; and Bethune et a/., Nature 1993, 363, 605-607].
  • These carbon nanotubes possess unique mechanical, electrical, thermal and optical properties, and such properties make them attractive for a wide variety of applications. See Baughman et a/., Science, 2002, 297, 787-792.
  • Methods of making CNTs include the following techniques: arc discharge [Ebbesen, Annu. Rev. Mater. Sci. 1994, 24, 235-264]; laser oven [Thess et ai, Science 1996, 273, 483-487]; flame synthesis [Vander Wal et ai, Chem. Phys. Lett. 2001, 349, 178-184]; and chemical vapor deposition [United States Patent No. 5,374,415], wherein a supported [Hafner et ai., Chem. Phys. Lett. 1998, 296, 195- 202] or an unsupported [Cheng et ai., Chem. Phys. Lett. 1998, 289, 602-610; Nikolaev et ai, Chem. Phys. Lett. 1999, 313, 91-97] metal catalyst may also be used.
  • Carbon nanotube chemistry has been described using a pyramidization angle formalism [Niyogi ef ai, Ace. of Chem. Res., 2002, 35, 1105-1113].
  • chemical reactivity and kinetic selectivity are related to the extent of s character due to the curvature-induced strain of the sp 2 -hybridized graphene sheet.
  • strain energy per carbon is inversely related to nanotube diameter, this model predicts smaller diameter nanotubes to be the most reactive, with the enthalpy of reaction decreasing as the curvature becomes infinite.
  • nanotubes have a reported van der Waals attraction of 0.5 eV per nanometer of tube-tube contact [O'Connell et ai, Chem. Phys. Lett. 2001, 342, 265-271; and Thess et ai, Science 1996, 273, 483-487].
  • the present invention is directed towards methods of thermally defunctionalizing functionalized (derivatized) carbon nanotubes (CNTs) in solution or while suspended in a liquid medium.
  • Such defunctionalization largely comprises the removal of sidewall functionality from the CNTs, but can also serve to remove functionality from the CNT ends.
  • Such methods allow for the resuspension of such defunctionalized CNTs in various solvents and permit the defunctionalization of functionalized CNTs that would normally decompose (or partially decompose) upon thermal treatment.
  • Such methods of defunctionalization can typically lead to defunctionalized CNTs that are essentially pristine (or nearly pristine), and which, in contrast to prior art methods of thermal defunctionalization, can be easily resuspended in a variety of solvents.
  • the methods of the present invention generally comprise the steps of: (a) suspending/dissolving a quantity of functionalized CNTs in a solvent to form a suspension/solution of functionalized CNTs; and (b) heating said suspension/solution to a temperature that will thermally defunctionalize the functionalized CNTs yielding a defunctionalized product. Temperatures exceeding the atmospheric pressure boiling point of the solvent are easily achieved by sealing the mixture in a closed pressure vessel.
  • the methods of the present invention are flexible in that they work with a variety of different kinds of functionalized CNTs, and they can employ a variety of different solvents.
  • the functionalized CNTs have been partially and/or selectively functionalized (e.g., by electronic type).
  • the solvent selection is directed by the kinds of functionalized CNTs being defunctionalized.
  • the defunctionalization is used to render a partially defunctionalized product.
  • the defunctionalization can be homogeneous.
  • Such partial defunctionalization can lead to functionalized CNTs with stoichiometries that might otherwise be unattainable with direct functionalization methods.
  • one or more analytical techniques are used to evaluate the defunctionalized product. Such techniques can be used to determine the extent of defunctionalization and the extent to which the defunctionalized CNTs have been returned to their pristine (original) state.
  • SWNTs single- wall carbon nanotubes
  • FIGURE 1 illustrates two reaction schemes by which SWNTs can be functionalized by diazonium species, where in reaction 1 the diazonium species is generated in situ under solvent free conditions, and where in reaction 2 the diazonium species is added directly to a surfactant-aided suspension of SWNTs;
  • FIGURE 2 depicts a thermogravimetric analysis (TGA) plot of the thermal defunctionalization of heavily functionalized (4-chlorophenyl) SWNTs in the dry state;
  • TGA thermogravimetric analysis
  • FIGURES 3 A-E depict Raman spectra (taken with 633 nm excitation) of (A) pristine (unreacted) SWNTs, (B) heavily functionalized SWNTs containing 4- chlorophenyl addends by treatment of micelle-coated SWNTs with 4- chlorobenzenediazonium tetrafluoroborate and corresponding to the material used for the TGA in FIGURE 2, (C) the same material as in 3B, but after neat thermal treatment at 10°C/min to 650°C in Ar, (D) the same material as in 3B, but after neat thermal treatment at 10°C/min to 450°C and holding at 450°C for 2 hours, and (E) the same material as in 3B, but after thermal defunctionalization in ortho- dichlorobenzene (ODCB) at 450°C for 3 hours; and
  • FIGURE 4 illustrates the thermolysis of 4-fett-butylphenyl-functionalized SWNTs (prepared by the SDS-coated SWNT/H 2 O protocol) in ODCB (solvent) that affords defunctionalized SWNTs and two discernable volatile products, the biphenyls 1 and 2, as determined by a GC-MS analysis of the reaction mixture.
  • the present invention is directed towards methods of thermally defunctionalizing functionalized (derivatized) carbon nanotubes (CNTs) in solution or suspended in a liquid medium.
  • Such defunctionalization is largely directed to the removal of sidewall functionality from the CNTs, but can also serve to remove functionality from the CNT ends.
  • Such methods allow for the resuspension of such defunctionalized CNTs in various solvents and permit the defunctionalization of functionalized CNTs that would normally decompose (or partially decompose) upon thermal treatment.
  • Such methods of defunctionalization can typically lead to defunctionalized CNTs that are essentially pristine (or nearly pristine), and which, in contrast to prior art methods of thermal defunctionalization, can be easily resuspended in a variety of solvents. Additionally, such solvent-based defunctionalization can partially defunctionalize functionalized CNTs in a generally homogeneous manner.
  • the methods of the present invention generally comprise the steps of: (a) dissolving or suspending a quantity of functionalized CNTs in a solvent to form a solution/suspension of functionalized CNTs; and (b) heating said solution/suspension to a temperature that will thermally defunctionalize the functionalized CNTs to yield a defunctionalized product.
  • CNTs include, but are not limited to, single-wall carbon nanotubes (SWNTs), multi-wall carbon nanotubes (MWNTs), double-wall carbon nanotubes (DWNTs), buckytubes, fullerene tubes, tubular fullerenes, graphite fibrils, and combinations thereof.
  • SWNTs single-wall carbon nanotubes
  • MWNTs multi-wall carbon nanotubes
  • DWNTs double-wall carbon nanotubes
  • buckytubes fullerene tubes, tubular fullerenes, graphite fibrils, and combinations thereof.
  • Such CNTs can initially be of a variety and range of lengths, diameters, number of tube walls, chiralities (helicities), etc., and can generally be made by any known technique.
  • the terms "carbon nanotube” and “nanotube” will be used interchangeably herein.
  • Such CNTs are often subjected to one or more purification steps [see, e.g., Chiang et al.,
  • Functionalized CNTs can be chemically functionalized derivatives of any of the above-mentioned kinds or types of CNTs.
  • Chemically functionalized is the chemical attachment (typically via covalent bonding) of functional moieties to the sidewalls and/or ends of CNTs.
  • suitably functionalized CNTs include, but are not limited to, those described in the following references: Liu et ai, Science, 1998, 280, 1253-1256; Chen et ai, Science, 1998, 282, 95-98; Holzinger et ai, Angew. Chem. Int. Ed., 2001, 40, 4002-4005; Khabashesku et ai, Ace. Chem. Res., 2002, 35, 1087-1095; International Patent Publication Number WO 02/060812, filed January 29, 2002; Bahr et ai, J. Am. Chem. Soc. 2001, 123, 6536-6542; Bahr et ai, Chem. Mater.
  • solvents employed in the methods of the present invention are thermally stable at the temperatures required for defunctionalization of the functionalized CNTs.
  • the solvent selection is directed by the kinds of functionalized CNTs being defunctionalized.
  • Suitable solvents include, but are not limited to, o-dichlorobenzene (ODCB), benzene, toluene, water, sulfuric acid, oleum (sulfuric acid with dissolved sulfur trioxide), sulfuric acid with dissolved potassium persulfate or other radical initiator such as peroxide, liquid ammonia, liquid ammonia with dissolved alkali metals, alkanes, parafins, thiophene, and combinations thereof.
  • ODCB o-dichlorobenzene
  • benzene toluene
  • water sulfuric acid
  • oleum sulfuric acid with dissolved sulfur trioxide
  • sulfuric acid with dissolved potassium persulfate or other radical initiator such as peroxide, liquid ammonia,
  • the functionalized CNTs are further polymer- wrapped and/or surfactant suspended in the solvent or liquid medium prior to being defunctionalized.
  • such polymer wrapping and/or surfactants can serve to keep the CNTs in suspension after they have been completely or partially defunctionalized. See O'Connell et ai, Chem. Phys. Lett., 2001, 342, 265-271; and O'Connell et ai, Science, 2002, 297, 593-596 for exemplary methods of polymer wrapping and surfactant suspending CNTs, respectively.
  • the solvent includes a polymer such that the defunctionalization is carried out while in a polymer matrix and thereby provides a blended polymer/pristine nanotube sample after defunctionalization and upon removal of the solvent.
  • the functionalized CNTs are dispersed directly in a polymer matrix, then defunctionalized to yield a product blend comprising unfunctionalized CNTs in a polymer host. Such product blends benefit from the greater dispersability of the functionalized CNTs (relative to unfunctionalized CNTs) in the polymer host.
  • the temperatures required for thermal defunctionalization vary depending on the type(s) of functionalized CNTs being defunctionalized. Typically, such defunctionalization temperatures range from about 100°C to about 700°C, and more typically from about 250°C to about 400°C. In some embodiments, a ramped or variable heating process is used.
  • Heating a solution or suspension of functionalized CNTs to a temperature required for complete or partial thermal defunctionalization can be accomplished via a variety of heating methods. Suitable heating methods include, but are not limited to, heating mantles, immersion heaters, microwave heating, and combinations thereof.
  • the heating is carried out with stirring, or some other kind of agitation, to ensure homogeneous thermolysis by minimizing thermal gradients within the suspension.
  • the thermal defunctionalization process entails a defunctionalization duration, lasting between about 3 minutes and about 2 days, and more typically between about 30 minutes and about 3 hours, during which time the functionalized CNTs are heated.
  • the functionalized CNTs are only partially defunctionalized. This permits product stoichiometries of such partially defunctionalized CNTs that might otherwise not be achievable.
  • partial defunctionalization is a result of selective thermal defunctionalization according to (n,m) type, with differing types having differing propensities to defunctionalize.
  • the CNTs upon being fully or partially defunctionalized, flocculate or fall out of suspension/solution.
  • the defunctionalization is carried out in a sealed reaction vessel. In some embodiments, these sealed reaction vessels permit the use of temperatures that exceed the atmospheric pressure boiling point of the solvent. In some embodiments, some of the defunctionalization products are volatile. In some embodiments, the defunctionalization products react with the suspension/solution medium.
  • one or more analytical techniques are used to evaluate the defunctionalized product and/or byproducts. Such techniques can be used to determine the extent of defunctionalization and the extent to which the defunctionalized carbon nanotubes have been returned to their pristine (original) state.
  • the liquid defunctionalization medium can be analyzed with gas chromatography-mass spectrometry (GC-MS) or other suitable analytical techniques.
  • GC-MS gas chromatography-mass spectrometry
  • the defunctionalized product is only partially defunctionalized, whereas in other embodiments it is completely defunctionalized.
  • the completely defunctionalized CNTs are essentially in their pristine (or nearly pristine) state.
  • An important aspect of the methods described herein is that the defunctionalized CNTs of the present invention (i.e., solvent defunctionalized CNTs) can be redispersed much more easily than CNTs that have been thermally defunctionalized in the dry state.
  • the wholly or partially defunctionalized CNTs of the present invention are redispersed in solvents with the aid of surfactants and/or polymers.
  • such wholly or partially defunctionalized CNTs can be manipulated in essentially any manner in which pristine CNTs can be manipulated.
  • CNTs carbon nanotubes
  • bonding e.g., covalently
  • the present invention does not render the defunctionalized carbon nanotubes unsuspendable/insoluble from that point on.
  • solvent-based defunctionalization methods of the present invention mitigate both the packing of the CNTs into ordered bundles and, possibly, cross-linking which is thought to occur between such functionalized CNTs when they are heated in the dry state.
  • This Example serves to illustrate how CNTs can be functionalized with diazonium chemistry in accordance with some embodiments of the present invention.
  • diazonium species can be generated in situ (reaction 1), or added directly (reaction 2), to SWNTs to render them functionalized.
  • Reaction 1 is carried out without any solvent [see Dyke et ai, J. Am. Chem. Soc, 2003, 125, 1156-1157], and in reaction 2, the SWNTs are first dispersed in water with sodium dodecylsulfate (SDS) [see Dyke et ai, Nano Lett. 2003, 3, 1215-1218].
  • SDS sodium dodecylsulfate
  • SWNTs were functionalized with 4- clorophenylene addends in accordance with reaction 2 in FIGURE 1.
  • This Example serves to illustrate how functionalized CNTs can be thermally defunctionalized in solution/suspension in accordance with embodiments of the present invention.
  • SWNTs purified HiPco, obtained from Rice University's Carbon Nanotechnology Laboratory
  • ODCB otffto-dichlorobenzene
  • the reaction vessel was purged with nitrogen and sealed with a TEFLON cap.
  • the solution was heated in a sand bath placed inside a heating mantle at approximately 450°C with stirring for about 3 hours. After such time, the solution was cooled to room temperature.
  • the regenerated, defunctionalized SWNTs were then filtered through a TEFLON membrane and collected.
  • This Example serves to illustrate prior art methods of thermally defunctionalizing functionalized CNTs in the dry state.
  • thermogravimetric analysis (TGA) of heavily functionalized (4-chlorophenyl) nanotubes showed 49% weight loss, which corresponds to 1 in 9 carbons on the nanotube bearing an aryl moiety.
  • the addends appear to be removed in two separate thermal regions, one at 200-400°C and a second at 475-550°C. While not intending to be bound by theory, this might be indicative of compressed bands of functionalization vs. dispersed addend regions, or of the defunctionalization temperatures needed for addend expulsion on semiconducting vs. metallic tubes.
  • This Example serves to illustrate how Raman spectroscopy can be used to probe the defunctionalization of functionalized CNTs in both the solvent-based and dry state methods.
  • the thermal treatment of functionalized CNT material while dispersed in a solvent such as ODCB possibly prevents nanotube radicals from combining to form nanotube dimers; instead, two radicals on the same nanotube might combine by extended conjugation to regenerate the C-C double-bond. Conversely, extensive rebundling might be minimized under such solvent-based conditions.
  • solvent-based thermal defunctionalization the byproducts of a ODCB-thermalized reaction of 4-fett-butylphenyl functionalized SWNTs were examined by GC-MS analysis of the ODCB solution.

Abstract

La présente invention a trait à des procédés de défonctionnalisation thermique de nanotubes de carbone fonctionnalisés (soumis à une dérivatisation) en solution ou suspendus dans un milieu liquide. Une telle défonctionnalisation comprend substantiellement l'élimination de la fonctionnalité latérale des nanotubes de carbone, mais peut également être utilisé pour l'élimination de fonctionnalité des extrémités des nanotubes de carbone. De tels procédés facilitent la resuspension de tels nanotubes de carbone fonctionnalisés dans divers solvants et permettent la défonctionnalisation de nanotubes fonctionnalisés qui se décomposeraient normalement (ou partiellement) lors d'un traitement thermique. De tels procédés de défonctionnalisation peuvent typiquement permettre l'obtention de nanotubes défonctionnalisés qui sont essentiellement vierges (ou presque vierges), et qui, contrairement aux procédés de défonctionnalisation de l'art antérieur, peuvent faire l'objet d'une resuspension dans une variété de solvants.
PCT/US2004/035894 2003-10-31 2004-10-28 Traitement thermique de nanotubes de carbone fonctionnalises en solution pour effectuer leur defonctionnalisation WO2005049488A2 (fr)

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Cited By (2)

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WO2005012172A2 (fr) * 2003-07-29 2005-02-10 William Marsh Rice University Fonctionnalisation selective de nanotubes de carbone
KR20220128932A (ko) 2021-03-15 2022-09-22 주식회사 비츠로셀 향상된 전기 및 이온 전도도를 갖는 리튬 전지용 전극 제조 방법

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KR20220128932A (ko) 2021-03-15 2022-09-22 주식회사 비츠로셀 향상된 전기 및 이온 전도도를 갖는 리튬 전지용 전극 제조 방법

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