US20040034177A1 - Polymer and method for using the polymer for solubilizing nanotubes - Google Patents

Polymer and method for using the polymer for solubilizing nanotubes Download PDF

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US20040034177A1
US20040034177A1 US10/255,122 US25512202A US2004034177A1 US 20040034177 A1 US20040034177 A1 US 20040034177A1 US 25512202 A US25512202 A US 25512202A US 2004034177 A1 US2004034177 A1 US 2004034177A1
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polymer
nanotube
carbon
solubilizing
swnts
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Jian Chen
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Zyvex Performance Materials LLC
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Priority to AT03252761T priority patent/ATE498582T1/de
Priority to EP03252761A priority patent/EP1359121B1/fr
Priority to DE60336032T priority patent/DE60336032D1/de
Priority to JP2003127132A priority patent/JP2004002850A/ja
Priority to KR1020030029184A priority patent/KR100582330B1/ko
Publication of US20040034177A1 publication Critical patent/US20040034177A1/en
Priority to US10/895,161 priority patent/US7244407B2/en
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    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/158—Carbon nanotubes
    • C01B32/168—After-treatment
    • C01B32/174—Derivatisation; Solubilisation; Dispersion in solvents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • B82B1/00—Nanostructures formed by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
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    • C01B2202/00—Structure or properties of carbon nanotubes
    • C01B2202/02—Single-walled nanotubes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2918—Rod, strand, filament or fiber including free carbon or carbide or therewith [not as steel]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2973—Particular cross section
    • Y10T428/2975—Tubular or cellular
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/30—Self-sustaining carbon mass or layer with impregnant or other layer

Definitions

  • the present invention is related to solubilization of nonotubes, and more particularly to a polymer that is capable of solubilizing nanotubes.
  • a carbon nanotube can be visualized as a sheet of hexagonal graph paper rolled up into a seamless tube and joined.
  • Each line on the graph paper represents a carbon-carbon bond, and each intersection point represents a carbon atom.
  • carbon nanotubes are elongated tubular bodies which are typically only a few atoms in circumference.
  • the carbon nanotubes are hollow and have a linear fullerene structure.
  • the length of the carbon nanotubes potentially may be millions of times greater than their molecular-sized diameter.
  • SWNTs single-walled carbon nanotubes
  • MWNTs multi-walled carbon nanotubes
  • Carbon nanotubes are currently being proposed for a number of applications since they possess a very desirable and unique combination of physical properties relating to, for example, strength and weight. Carbon nanotubes have also demonstrated electrical conductivity. See Yakobson, B. I., et al., American Principle, 85, (1997), 324-337; and Dresselhaus, M. S., et al., Science of Fullerenes and Carbon Nanotubes, 1996, San Diego: Academic Press, pp. 902-905. For example, carbon nanotubes conduct heat and electricity better than copper or gold and have 100 times the tensile strength of steel, with only a sixth of the weight of steel. Carbon nanotubes may be produced having extraordinarily small size. For example, carbon nanotubes are being produced that are approximately the size of a DNA double helix (or approximately ⁇ fraction (1/50,000) ⁇ th the width of a human hair).
  • carbon nanotubes are well suited for a variety of uses, from the building of computer circuits to the reinforcement of composite materials, and even to the delivery of medicine. As a result of their properties, carbon nanotubes may be useful in microelectronic device applications, for example, which often demand high thermal conductivity, small dimensions, and light weight.
  • One potential application of carbon nanotubes that has been recognized is their use in flat-panel displays that use electron field-emission technology (as carbon nanotubes can be good conductors and electron emitters).
  • Electrode shielding such as for cellular telephones and laptop computers, radar absorption for stealth aircraft, nano-electronics (including memories in new generations of computers), and use as high-strength, lightweight composites.
  • carbon nanotubes are potential candidates in the areas of electrochemical energy storage systems (e.g., lithium ion batteries) and gas storage systems.
  • the “laser vaporization” technique utilizes a pulsed laser to vaporize graphite in producing the carbon nanotubes.
  • the laser vaporization technique is further described by A. G. Rinzler et al. in Appl. Phys. A, 1998, 67, 29, the disclosure of which is hereby incorporated herein by reference.
  • the laser vaporization technique produces carbon nanotubes that have a diameter of approximately 1.1 to 1.3 nanometers (nm).
  • Such laser vaporization technique is generally a very low yield process, which requires a relatively long period of time to produce small quantities of carbon nanotubes. For instance, one hour of laser vaporization processing typically results in approximately 100 milligrams of carbon nanotubes.
  • SWNTs single-walled nanotubes
  • Ni:Y;C graphite powder
  • SWNTs are produced as close-packed bundles (or “ropes”) with such bundles having diameters ranging from 5 to 20 nm.
  • the SWNTs are well-aligned in a two-dimensional periodic triangular lattice bonded by van der Waals interactions.
  • the electric arc technique of producing carbon nanotubes is further described by C. Journet and P. Bernier in Appl. Phys. A, 67, 1, the disclosure of which is hereby incorporated herein by reference. Utilizing such an electric arc technique, the average carbon nanotube diameter is typically approximately 1.3 to 1.5 nm and the triangular lattice parameter is approximately 1.7 nm.
  • the electric arc production technique is generally a very low yield process that requires a relatively long period of time to produce small quantities of carbon nanotubes. For instance, one hour of electric arc processing typically results in approximately 100 milligrams of carbon nanotubes.
  • the gas phase technique which produces much greater quantities of carbon nanotubes than the laser vaporization and electric arc production techniques.
  • the gas phase technique which is referred to as the HiPcoTM process, produces carbon nanotubes utilizing a gas phase catalytic reaction.
  • the HiPco process uses basic industrial gas (carbon monoxide), under temperature and pressure conditions common in modern industrial plants to create relatively high quantities of high-purity carbon nanotubes that are essentially free of by-products.
  • the HiPco process is described in further detail by P. Nikolaev et al. in Chem. Phys. Lett., 1999, 313, 91, the disclosure of which is hereby incorporated herein by reference.
  • the HiPco process may enable daily product of carbon nanotube in quantities of a pound or more.
  • the HiPco technique produces carbon nanotubes that have relatively much smaller diameters than are typically produced in the laser vaporization or electric arc techniques.
  • the nanotubes produced by the HiPco technique generally have diameters of approximately 0.7 to 0.8 nm.
  • Covalent side-wall functionalizations of carbon nanotubes can lead to the dissolution of carbon nanotubes in organic solvents. It should be noted that the terms “dissolution” and “solubilization” are used interchangeably herein. See Boul, P. J. et al., Chem Phys. Lett. 1999, 310, 367 and Georgakilas, V. et al., J. Am. Chem. Soc. 2002, 124, 760-761, the disclosures of which are hereby incorporated herein by reference. The disadvantage of this approach is that a carbon nanotube's intrinsic properties are changed significantly by covalent side-wall functionalizations.
  • Carbon nanotubes can also be solubilized in organic solvents and water by polymer wrapping. See Dalton, A. B. et al., J. Phys. Chem. B 2000, 104, 10012-10016, Star, A. et al. Angew. Chem., Int. Ed. 2001, 40, 1721-1725, and O'Connell, M. J. et al. Chem. Phys. Lett. 2001, 342, 265-271, the disclosures of which are hereby incorporated herein by reference.
  • FIGS. 1 A- 1 C show examples of such polymer wrapping of a carbon nanotube. In polymer wrapping, a polymer “wraps” around the diameter of a carbon nanotube. For instance, FIG.
  • FIG. 1 shows an example of polymers 102 A and 102 B wrapping around single-walled carbon nanotube (SWNT) 101 .
  • FIG. 1B shows an example of polymer 103 A and 103 B wrapping around SWNT 101 .
  • FIG. 1C shows an example of polymers 104 A and 104 B wrapping around SWNT 101 . It should be noted that the polymers in each of the examples of FIGS. 1 A- 1 C are the same, and the FIGURES illustrate that the type of polymer-wrapping that occurs is random (e.g., the same polymers wrap about the carbon nanotube in different ways in each of FIGS. 1 A- 1 C).
  • SWNT HiPco is the only SWNT material that can be currently produced at a large scale with high purity.
  • the present invention is directed to a method for solubilizing nanotubes, a polymer for solubilizing nanotubes, and resulting compositions of matter that may be formed using solubilized nanotubes.
  • Embodiments of the present invention provide a new approach to solubilizing nanotubes, such as carbon nanotubes, in solvents.
  • the solvents can be, in principle, any solvents. Solubilization of carbon nanotubes in accordance with embodiments of the present invention have been experimentally demonstrated in organic solvents and in water.
  • carbon nanotube surfaces are functionalized in a non-wrapping fashion by functional conjugated polymers that include functional groups for solubilizing such nanotubes.
  • non-wrapping means not enveloping the diameter of a nanotube.
  • associating a polymer with a nanotube in a “non-wrapping fashion” encompasses any association of the polymer with the nanotube in which the polymer does not completely envelope the diameter of the nanotube.
  • the non-wrapping fashion may be further defined and/or restricted.
  • a polymer can associate with a nanotube (e.g., via ⁇ -stacking interaction therewith) wherein the polymer's backbone extends substantially along the length of the nanotube without any portion of the backbone extending over more than half of the nanotube's diameter in relation to any other portion of the polymer's backbone.
  • Various embodiments provide polymers that associate with carbon nanotubes in a non-wrapping fashion. More specifically, various embodiments of polymers are provided that comprise a relatively rigid backbone that is suitable for associating with a carbon nanotube substantially along the nanotube's length, as opposed to about its diameter. In preferred polymers, the major interaction between the polymer backbone and the nanotube surface is parallel ⁇ -stacking. Such interaction may result in the polymer non-covalently bonding (or otherwise associating) with the nanotube.
  • rigid functional conjugated polymers that may be utilized in embodiments of the present invention include, without limitation, poly(aryleneethynylene)s and poly(3-decylthiophene).
  • the polymers further comprise at least one functional extension from the backbone, wherein such at least one function extension comprises any of various desired functional groups that are suitable for solubilizing a carbon nanotube.
  • a method of solubilizing a nanotube comprises mixing a polymer with a nanotube, and the polymer noncovalently bonding with the nanotube in a non-wrapping fashion, wherein the polymer comprises at least one functional portion for solubilizing the nanotube.
  • mixing is intended to encompass “adding,” “combining,” and similar terms for presenting at least one polymer to at least one nanotube.
  • a polymer for solubilizing nanotubes comprises a backbone portion for noncovalently bonding with a nanotube in a non-wrapping fashion, and at least one functional portion for solubilizing the nanotube.
  • a process comprises mixing at least one polymer with at least one nanotube in a solvent.
  • the solvent may comprise an organic solvent, and in other embodiments the solvent may comprise an aqueous solvent. The mixing results in the at least one polymer forming a noncovalent bond with the at least one nanotube in a non-wrapping fashion, and the at least one polymer solubilizing the at least one nanotube.
  • a method of solubilizing carbon nanotubes comprises mixing at least one polymer with at least one carbon nanotube in a solvent.
  • the solvent may comprise an organic solvent, and in other embodiments the solvent may comprise an aqueous solvent.
  • the method further comprises the at least one polymer interacting with the at least one carbon nanotube's surface via ⁇ -stacking, and the at least one polymer solubilizing the at least one carbon nanotube.
  • FIGS. 1 A- 1 C show examples of polymer wrapping of carbon nanotubes of the prior art
  • FIGS. 2 A- 2 B show an example molecular model of a polymer that associates with a carbon nanotube in a non-wrapping fashion in accordance with an embodiment of the present invention
  • FIGS. 3 A- 3 C show example polymer structures of embodiments of the present invention.
  • FIG. 4 shows another example of a polymer structure that may be implemented for associating with a carbon nanotube in a non-wrapping fashion in accordance with an embodiment of the present invention
  • FIG. 5A shows a graph illustrating the thin film visible and near infrared (IR) spectra of SWNTs HiPco (without a polymer associated therewith);
  • FIG. 5B shows a graph illustrating the thin film visible and near IR spectra of SWNTs HiPco solubilized by an example polymer of an embodiment of the present invention
  • FIG. 6A shows a transmission electron microscopy (“TEM”) image of SWNTs laser (i.e., SWNTs produced by the laser technique) solubilized by an example polymer of an embodiment of the present invention
  • FIG. 6B shows a TEM image of SWNTs arc (i.e., SWNTs produced by the arc technique) solubilized by an example polymer of an embodiment of the present invention
  • FIGS. 6C and 6D show TEM images of SWNTs HiPco solubilized with an example polymer of an embodiment of the present invention
  • FIGS. 7A and 7B show high resolution TEM images of SWNTs laser solubilized with an example polymer of an embodiment of the present invention
  • FIGS. 8 A- 8 C show high resolution TEM images of SWNTs arc solubilized with an example polymer of an embodiment of the present invention.
  • FIG. 9 shows a field-emission scanning electron microscopy (“SEM”) image (1.00 kV) of a tom edge of Bucky paper formed in accordance with a solubilization technique of an embodiment of the present invention, which illustrates that the majority of the sample is SWNT nanoribbon.
  • SEM field-emission scanning electron microscopy
  • Embodiments of the present invention provide a new approach to solubilizing nanotubes in solvents.
  • certain embodiments of the present invention may enable solubilization in organic solvents, and certain embodiments may enable solubilization in aqueous solvents.
  • This approach is based on a discovery that carbon nanotube surfaces can be functionalized in a non-wrapping fashion by functional conjugated polymers. For instance, an example molecular model of a polymer that associates (e.g., noncovalently bonds) with a carbon nanotube in a non-wrapping fashion is shown in FIGS. 2 A- 2 B.
  • FIG. 2B is a cross-sectional view of FIG. 2A taken as indicated in FIG. 2A.
  • a carbon nanotube (and more specifically a single-walled carbon nanotube in this example) 201 has polymer 202 associated with it in a non-wrapping fashion therewith.
  • Polymer 202 comprises a relatively rigid backbone 203 that associates with carbon nanotube 201 substantially along the length, as opposed to about the diameter, of such carbon nanotube 201 .
  • polymer 202 associates with carbon nanotube 201 in a non-wrapping fashion, which is advantageous for various reasons, some of which are described more fully herein.
  • backbone 203 associates with nanotube 201 (e.g., via ⁇ -stacking interaction therewith) wherein such backbone 203 extends substantially along the length of nanotube 201 without any portion of backbone 203 extending over more than half of the diameter of nanotube 201 in relation to any other portion of backbone 203 .
  • backbone 203 is sufficiently rigid such that no portion thereof bends to the extent that such portion passes the half-diameter (or “equator line”) 205 of nanotube 201 relative to location 206 of nanotube 201 at which at least a portion of backbone 203 is associated with nanotube 201 .
  • backbones 203 may vary (e.g., certain implementations may enable a portion of backbone 203 to bend beyond half-diameter 205 while another portion of such backbone is arranged at location 206 of nanotube 201 ), but such backbones 203 are preferably sufficiently rigid such that they do not wrap (i.e., fully envelope the diameter of) nanotube 201 .
  • backbones 203 are preferably sufficiently rigid such that they do not wrap (i.e., fully envelope the diameter of) nanotube 201 .
  • portions of polymer 202 may extend about all or a portion of the diameter of nanotube 201 , but backbone 203 of polymer 202 is preferably sufficiently rigid such that it does not wrap about the diameter of nanotube 201 .
  • Polymer 202 further comprises various functional extensions from backbone 203 , such as functional extensions 204 A and 204 B, which may comprise any of various desired functional groups for functionalizing carbon nanotube 201 .
  • functional extensions 204 A and 204 B may comprise any of various desired functional groups for functionalizing carbon nanotube 201 .
  • embodiments of the present invention include functional groups in polymer 202 that are suitable for solubilizing carbon nanotube 201 .
  • polymer 202 associating with carbon nanotube 201 e.g., via r-stacking interaction
  • polymer 202 associating with carbon nanotube 201 e.g., via r-stacking interaction
  • functional groups such as functional extensions 204 A and 204 B
  • backbone 203 in a desired manner to accurately control the spacing of such functional groups.
  • functional groups such as functional extensions 204 A and 204 B
  • backbone 203 in a desired manner to accurately control the spacing of such functional groups.
  • it becomes much more difficult to control the relative spacing of the functional groups arranged on the polymer because their spacing is dependent on the wrapping of the polymer.
  • By controlling the spacing of such functional groups along backbone 202 more control may be provided over if/how the functional groups interact with each other, carbon nanotube 201 , and/or other elements to which the functional groups may be exposed.
  • carbon nanotubes possess a very desirable and unique combination of physical properties relating to, for example, strength, weight, electrical conductivity, etc. Having the ability to solubilize carbon nanotubes while preserving nearly all of the nanotubes' properties thus offers many possibilities in, for example, material science. For instance, in certain applications, carbon nanotubes may be solubilized and thus used in forming a desired composition of matter (or “material”) that has desired properties supplied at least in part by the nanotubes, some examples of which are described further below.
  • FIGS. 3 A- 3 C show example polymer structures of embodiments of the present invention.
  • FIG. 3A shows an example poly(aryleneethynylene) (labeled “1”) polymer structure that may be used to noncovalently bond with a carbon nanotube in a non-wrapping fashion.
  • the example polymer structure shown in FIG. 3A comprises functional extensions R 1 , R 2 , R 3 , and R 4 , which may, in alternative example implementations for solubilizing carbon nanotubes, be implemented as either 1a, 1b, 1c, or 1d shown hereafter:
  • FIG. 3B shows another example poly(aryleneethynylene) (labeled “3” and referred to herein as “3”) polymer structure that may be used to noncovalently bond with a carbon nanotube in a non-wrapping fashion.
  • FIG. 3C shows another example poly(aryleneethynylene) (labeled “4” and referred to herein as “4”) polymer structure that may be used to noncovalently bond with a carbon nanotube in a non-wrapping fashion.
  • the example polymer structures 1, 3, and 4 shown in FIGS. 3 A- 3 C are poly(phenyleneethynylene) structures, it should be understood that other poly(aryleneethynylene)-type structures may be used in accordance with embodiments of the present invention.
  • the example polymer structures of FIGS. 3 A- 3 C may be implemented for noncovalently bonding with a carbon nanotube in a non-wrapping fashion, as with the example shown in FIGS. 2 A- 2 B, for solubilizing such carbon nanotube.
  • the present invention is not intended to be limited solely to the functional groups of 1a, 1b, 1c, and 1d (or the functional groups of polymer structures 3 and 4) shown above for solubilizing carbon nanotubes, but rather any such functional group now known or later developed for solubilizing carbon nanotubes may be used in accordance with embodiments of the present invention.
  • the solubilizing functional group(s) included in the polymer do not substantially alter the intrinsic properties of the carbon nanotube.
  • FIG. 4 shows another example of a polymer structure that may be implemented for noncovalently bonding with a carbon nanotube in a non-wrapping fashion. More specifically, FIG. 4 shows an example structure of a highly regioregular head-to-tail poly(3-decylthiophene) (labeled “2”) that may be implemented in certain embodiments of the present invention.
  • the backbone of 1, 2, 3, and 4 described above is rigid and cannot wrap around the SWNTs, and the major interaction between the polymer backbone and the nanotube surface is parallel ⁇ -stacking.
  • the example backbones 5-18 described below are also rigid such that they do not wrap around the nanotube, and the major interaction between such polymer backbones and the nanotube surface is parallel ⁇ -stacking.
  • Parallel ⁇ -stacking is one type of noncovalent bonding. See Chen, R. J. et al., J. Am. Chem.
  • SWNTs can be readily solubilized in CHCl 3 by mixing with 1 (e.g., 1a, 1b, 1c, or 1d), 2, 3, or 4 after vigorous shaking and/or bath-sonication.
  • the minimum weight ratio (WR initial ) of 1:SWNTs HiPco , 2:SWNTs HiPco , 3:SWNTs HiPco , and 4:SWNTs HiPco required to solubilize the SWNTs HiPco (i.e., SWNTs produced by the HiPco technique) is about 0.4; and the maximum concentration of SWNTs HiPco in CHCl 3 is about 5 mg/ml for 1d, which represents the highest solubility of SWNTs HiPco in organic solvents by noncovalent functionalization.
  • SWNTs Hipco can be dissolved in 6.8 ml of CHCl 3 in the presence of 5.4 mg of 1a; and 20.4 mg of SWNTs HiPco can be dissolved in 4.0 ml of CHCl 3 in the presence of 20.4 mg of 1d.
  • the maximum concentration of SWNTs laser (i.e., SWNTs produced by the laser technique) and SWNTs arc (i.e., SWNTs produced by the arc technique) is about 0.5 mg/ml for 1a.
  • the solubility of SWNTs can be further improved by optimizing the polymer side chain's length and composition. For example, the longer side chains and/or the side chains with branched structures can further improve the solubility of the SWNTs.
  • SWNTs can be readily solubilized in deionized water by mixing with 4 after bath-sonication.
  • 13.7 mg of SWNTs HiPco can be dissolved in 6.9 ml of deionized water in the presence of 13.7 mg of 4.
  • SWNTs HiPco purified HiPco-SWNTs
  • SWNTs laser purified laser-grown SWNTs
  • SWNTs arc purified electric arc-grown SWNTs
  • the weight ratio (WR final ) of 1a:SWNTs HiPco in the final product is estimated to be about 0.38-0.40, which is independent of WR initial .
  • FIG. 5A shows a graph illustrating the thin film visible and near infrared (IR) spectra of SWNTs HiPco (without a polymer associated therewith).
  • FIG. 5B shows a graph illustrating the thin film visible and near IR spectra of 1a-SWNTs HiPco .
  • the band structures of 1a-SWNTs HiPco are very similar to those of pristine SWNTs HiPco (of FIG.
  • the resulting bucky paper dissolves more slowly in CHCl 3 at a lower concentration (approximately 0.1-0.2 mg/ml of 1a-SWNTs HiPco in CHCl 3 ).
  • concentration approximately 0.1-0.2 mg/ml of 1a-SWNTs HiPco in CHCl 3 .
  • n is preferably greater than or equal to 2
  • R represents any organic functional group, such as R ⁇ OC 10 H 21 , R ⁇ C 10 H 21 , or other functional group described herein for solubilizing nanotubes, as examples.
  • the example backbones 5-15 are poly (aryleneethynylene)s, backbone 16 is a polyphenylene, backbone 17 is a polypyrrole, and backbone 18 is a polythiophene.
  • the 1-SWNTs HiPco solution of a preferred embodiment can mix homogeneously with other polymer solutions such as polycarbonate and polystyrene.
  • Homogeneous nanotube-polycarbonate and -polystyrene composites can be prepared by removing the organic solvents.
  • Soluble 1a-SWNTs HiPco complex significantly improves the mechanical properties of commercial polymers.
  • the tensile strength and break strain of pure poly(bisphenol A carbonate) are 26 MPa and 1.23%, respectively; 3.8 wt % of SWNTs HiPco filling results in 68% and 1800% increases in tensile strength (43.7 MPa) and break strain (19.1%) of poly(bisphenol A carbonate) (average M W approximately 64,000), respectively.
  • FIGS. 6 A- 6 D, 7 A- 7 B, and 8 A- 8 C show transmission electron microscopy (TEM) images
  • FIG. 9 shows a field emission scanning electron microscopy (SEM) image, which are described further hereafter. More specifically, FIG. 6A shows a TEM image of 1-SWNTs laser
  • FIG. 6B shows a TEM image of 1-SWNTs arc
  • FIGS. 6C and 6D show TEM images of 1-SWNTs HiPco .
  • the scale bar shown in FIGS. 6 A- 6 D is 100 nm.
  • FIGS. 7A and 7B show high resolution TEM images of 1a-SWNTs laser (120 kV, one drop of the freshly prepared chlorobenzene solution of 1a-SWNTs laser (approximately 0.05 mg/ml) was placed on a Holey Carbon 400 mesh TEM grid (SPI Supplies, Formvar coating was removed) in contact with a Kimwipes wiper. The solvent was quickly soaked away by the wiper, preventing the aggregation of nanotubes).
  • the scale bar shown in FIGS. 7 A- 7 B is 5 nm.
  • FIGS. 8 A- 8 C show high resolution TEM images of 1a-SWNTs arc (120 kV, one drop of the freshly prepared chlorobenzene solution of 1a-SWNTs arc (approximately 0.05 mg/ml) was placed on a Holey Carbon 400 mesh TEM grid (SPI Supplies, Formvar coating was removed) in contact with a Kimwipes wiper. The solvent was quickly soaked away by the wiper, preventing the aggregation of nanotubes).
  • the scale bar shown in FIGS. 8 A- 8 C is 5 nm.
  • FIG. 9 shows field-emission SEM image (1.00 kV) of a torn edge of Bucky paper (1a-SWNTs HiPco ), illustrating that the majority of sample is SWNT nanoribbon.
  • the TEM images show that the majority of SWNTs in 1a-SWNTs laser and 1a-SWNTs arc are small ropes (2-6 nm, see FIGS. 6A, 6B, 7 A, 7 B, and 8 A- 8 C), whereas the majority of SWNTs in 1a-SWNTs HiPco are nanoribbon assemblies of small ropes (see FIGS. 6C, 6D, and 9 ).
  • FIGS. 6C, 6D, and 9 The observation of a twisted SWNT nanoribbon on TEM grid surface shown in FIG.
  • 6D is indicative of the robustness of such two dimensional (2D) assemblies and further supports a ⁇ -stacking interaction with the polymer backbone oriented along the nanotube's length.
  • Such nanoribbon is indicative of robustness because if the 2D assembly is not robust, it will easily collapse into small ropes on the TEM grid surface. It should be possible to prevent such 2D assembly and obtain small ropes and/or individual SWNTs HiPco by using 1, for example, with bulky and/or ionic functional groups in the end of the side chains.
  • embodiments of the present invention provide a molecular structure that is capable of noncovalently bonding with a nanotube (e.g., carbon nanotube) in a non-wrapping manner, and the molecular structure may comprise one or more functional groups for solubilizing the nanotube to which the molecular structure associates.
  • the molecular structure forms a non-covalent bond with the nanotube; however, in certain implementations the molecular structure may be such that it forms a covalent bond with the nanotube in a non-wrapping fashion.
  • Solubilization of nanotubes allows for their use in enhancing the properties of various compositions of matter, including, as one example, plastics.
  • Insoluble nanotubes cannot be dispersed homogeneously in commercial plastics and adhesives; therefore the polymer composites made by the addition of insoluble nanotubes gave little improvement in mechanical performance of plastics (Ajayan, P. M. et al., Adv. Mater. 2000, 12, 750; Schadler, L. S. et al. Appl. Phys. Lett. 1998, 73, 3842).
  • soluble nanotubes can significantly improve the mechanical performance of plastics, for example.
  • the tensile strength and break strain of pure poly(bisphenol A carbonate) are 26 MPa and 1.23%, respectively; 3.8 wt % of SWNTs HiPco filling results in 68% and 1800% increases in tensile strength (43.7 MPa) and break strain (19.1%) of poly(bisphenol A carbonate) (average M W approximately 64,000), respectively.
  • Nanotubes may be formed from various materials such as, for example, carbon, boron nitride, and composites thereof.
  • the nanotubes may be single-walled nanotubes or multi-walled nanotubes.
  • MWNTs multi-walled carbon nanotubes
  • boron nitride nanotubes and composites thereof.
  • nanotubes is not limited solely to carbon nanotubes. Rather, the term “nanotubes” is used broadly herein and, unless otherwise qualified, is intended to encompass any type of nanotube now known or later developed.

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DE60336032T DE60336032D1 (de) 2002-05-02 2003-05-01 Polymer und Verfahren zum Lösen von Nanoröhren mit Hilfe dieses Polymers
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US20080194737A1 (en) 2008-08-14
US20040266939A1 (en) 2004-12-30
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