Process for derivatizing carbon nanotubes with diazonium species and compositions thereof

A carbon nanotube, single-wall carbon nanotube technology, applied in the direction of carbon nanotubes, single-walled carbon nanotubes, carbon compounds, etc., can solve problems such as obstruction and the existence of a large amount of graphite

Inactive Publication Date: 2007-04-11
RICE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other attempts at sidewall modification have also been made, all hampered by the presence of large amounts of graphite or amorphous carbon impurities

Method used

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  • Process for derivatizing carbon nanotubes with diazonium species and compositions thereof
  • Process for derivatizing carbon nanotubes with diazonium species and compositions thereof
  • Process for derivatizing carbon nanotubes with diazonium species and compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-11

[0050] For the electrochemical derivatization experiments, a piece of "Bucky paper" obtained by filtering the suspension was used as the working electrode of the three-electrode cell, immersed in the acetonitrile solution containing the diazonium salt and the electrolyte. The diazonium salts may be reduced to aryl radicals on the Baker paper surface, which subsequently form covalent bonds with the nanotubes. There is a lot of data on the conductivity of single-walled carbon nanotubes. In general, aryl diazonium salts are readily prepared under conditions that allow for a wide variety of functional groups. Thus, the method described here allows the functionalization of nanotubes with a wide variety of diazonium salts, including those that provide chemical treatments for re-elaboration after attachment to the nanotubes.

[0051] The purified single-walled nanotubes (herein referred to as SWNT-p) employed in this study contained little amorphous carbon or other exotic carbon imp...

Embodiment 12-17

[0106] The nanotubes used in this study are still prepared by the gas-phase catalytic method developed by Smalley et al. and are now commercially available (Carbon Nanotechnology, HiPco Materials). The method for the purification of production raw materials is to oxidize in humid air at 250°C for 24 hours, then stir in concentrated hydrochloric acid at room temperature for 24 hours, the formed material is first washed with a large amount of water, then with 10% aqueous sodium bicarbonate solution, Wash again with water. After vacuum drying, the material was ready for functionalization reactions.

[0107] Figure 12 shows the sequence of reactions. In a typical test, about 8 mg of single-walled carbon nanotubes were placed in 10 ml of 1,2-dichlorobenzene (ODCB) and ultrasonically oscillated for 10 minutes. Add the solution of aniline derivative (2.6mmol, about 4 g equivalent / mole carbon) in 5ml of acetonitrile to this suspension, transfer the feed solution to the reaction tube...

Embodiment 18

[0119] Derivatization reactions with aryldiazonium salts can also be induced photochemically. The photochemical reaction can also be carried out with the tetrafluoroborate 4-chlorobenzene diazonium salt adopted and prepared in Example 2. Therefore, a suspension of SWNT-p in 1,2-dichlorobenzene was generated by sonication. To this suspension was added a portion of the diazonium salt dissolved in a minimal amount of acetonitrile. The obtained mixed solution is placed in a photochemical reaction chamber for stirring. The excitation wavelength is 254nm (ultraviolet light source). The light source used for the photochemically induced reaction can be light of any wavelength, usually ultraviolet light or visible light. Figure 15 shows this reaction. The resulting material was similar in all respects to SWNT-2 prepared electrochemically according to the present invention.

[0120] This experiment further confirms that the reaction of diazonium salt leads to covalent attachment to...

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Abstract

The invention incorporates new processes for the chemical modification of carbon nanotubes. Such processes involve the derivatization of multi- and single-wall carbon nanotubes, including small diameter (ca. 0.7 nm) single-wall carbon nanotubes, with diazonium species. The method allows the chemical attachment of a variety of organic compounds to the side and ends of carbon nanotubes. These chemically modified nanotubes have applications in polymer composite materials, molecular electronic applications, and sensor devices. The methods of derivatization include electrochemical induced reactions, thermally induced reactions (via in-situ generation of diazonium compounds or pre-formed diazonium compounds), and photochemically induced reactions. The derivatization causes significant changes in the spectroscopic properties of the nanotubes. The estimated degree of functionality is ca. 1 out of every 20 to 30 carbons in a nanotube bearing a functionality moiety. Such electrochemical reduction processes can be adapted to apply site-selective chemical functionalization of nanotubes. Moreover, when modified with suitable chemical groups, the derivatized nanotubes are chemically compatible with a polymer matrix, allowing transfer of the properties of the nanotubes (such as, mechanical strength or electrical conductivity) to the properties of the composite material as a whole. Furthermore, when modified with suitable chemical groups, the groups can be polymerized to form a polymer that includes carbon nanotubes.

Description

[0001] This invention was made in connection with research under Grant No. NASA-JSC-NCC 9-77 from the National Aeronautics and Space Administration, No. NSR-DMR-0073046 from the National Science Foundation and No. NO0014-99-1-0406 from DARPA / ONR related. field of invention [0002] The present invention generally relates to carbon nanotubes. More specifically, the present invention relates to carbon nanotubes derivatized with diazo compounds, and uses of the derivatized carbon nanotubes. Background of the invention [0003] Fullerenes are all composed of SP 2 Closed cage molecules composed of hybridized carbons arranged in hexagonal and pentagonal shapes. Fullerenes (such as C 60 ) was initially seen as a closed spherical cage formed by the condensation of carbon vapor. Fullerene tubes are generated by preparing spherical fullerenes from carbon vapor by carbon arc method to deposit carbon on the cathode (Ebbesen et al. (Ebbesen I), "Large-Scale Synthesis of Carbon Nanotu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): D01F9/12C01B31/02C07C245/20C08K9/04C09C1/56
CPCC01P2002/86C09C1/56B82Y30/00C01B2202/02C01B31/0273B82Y40/00C08K9/04C09C1/565C01P2002/88C01B2202/36C01P2004/04C01B32/174B82B3/00
Inventor J·M·图尔J·L·巴尔杨季平
Owner RICE UNIV
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