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Compositions comprising functionalized carbon-based nanostructures and related methods

a carbon-based nanostructure and functional technology, applied in the direction of organic compounds/hydrides/coordination complexes, organic compounds, iron organic compounds, etc., can solve the problems of intrinsic limitation of thermal and/or electrochemical boundaries of devices, the labile nature of such chemical functionalities is significant drawback to the current available technology, and the material generally cannot survive further thermal, electrochemical and/or chemical treatment of graphene-based materials. , to achieve the effect of reducing the amount of an

Inactive Publication Date: 2012-07-05
MASSACHUSETTS INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides compositions and methods for functionalizing carbon-based nanostructures with various functional groups. These functional groups can have various structures and can be used to modify the properties of the carbon-based nanostructures. The functional groups can also be used to capture and reduce the amount of certain species in a sample. The technical effects of this invention include improved functionalization of carbon-based nanostructures and improved methods for reducing the amount of certain species in a sample.

Problems solved by technology

Moreover, current methodology often introduces basal plane functionalities that are weakly bound to the graphene surface through carbon-oxygen (C—O) or carbon-nitrogen (C—N) bonds and therefore, the resulting material generally cannot survive further thermal, electrochemical, and / or chemical treatment of the graphene-based material.
The labile nature of such chemical functionalities represents a significant drawback to the currently available technology, as in many cases it is necessary to deoxygenate the graphene derivatives under relatively harsh conditions to reestablish electrical conductivity within the graphene nanosheet.
Additionally, incorporation of these C—O or C—N modified graphene materials into devices can intrinsically limit the thermal and / or electrochemical boundaries of the device.

Method used

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  • Compositions comprising functionalized carbon-based nanostructures and related methods
  • Compositions comprising functionalized carbon-based nanostructures and related methods
  • Compositions comprising functionalized carbon-based nanostructures and related methods

Examples

Experimental program
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example 1

[0140]The following example describes the direct conversion of carbon-oxygen bonds on a graphite oxide basal plane to carbon bound carbonyl groups (e.g., see FIG. 10). GO (graphene oxide) in this example was functionalized using a Claisen rearrangement to allylically transpose tertiary alcohol functional groups found throughout the basal plane of graphite oxide into carbon-bound carbonyl derivatives. In traditional Claisen rearrangements, a vinyl allyl alcohol is heated to simultaneously break a carbon-oxygen bond while forming a carbon-carbon bond (via a sigmatropic rearrangement). In this example the tertiary alcohols that adorn the surface of graphite oxide function as the tertiary allylic alcohols. Direct treatment of these functional groups with a vinyl group equivalent (e.g., dimethylacetamide dimethylacetal is shown in FIG. 10) forms a vinyl allyl alcohol on GO, in situ. Heating this modified GO then directly breaks the tertiary alcohol bond and allylically forms a new carbon...

example 2

[0145]The following example described characterization of functionalized nanostructures formed using and / or comprising certain compositions of the present invention.

[0146]Reaction conditions for this example are substantially similar as described in Example 1, except for variations in the solvent and temperature. In addition, control reactions were carried out (e.g., wherein no DMADMA was added to the reaction mixture).

[0147]In this example, the following abbreviations are employed, and are further described herein:

rGO1—reaction in THF at 60° C., DMADMA added

rGO1c—control reaction in THF at 60° C., no DMADMA added

rGO2—reaction in 1,4-dioxane at 100° C., DMADMA added

rGO2c—control reaction in 1,4-dioxane at 100° C., no DMADMA added

rGO3—reaction in diglyme at 150° C., DMADMA added

rGO3c—control reaction in diglyme at 150° C., no DMADMA added)

rGO3b—reaction in diglyme sonicated for 3 h at pH=9

rGO3b (500)—sample annealed in 500° C. for 6 h in N2 atmosphere

[0148]Characterization: Throughou...

example 3

[0156]The following example describes the synthesis of allylic amide-functionalized graphene. (FIGS. 11A-B). As shown in FIG. 11C, after 1 hour of reacting graphene oxide with [(CH3)2N]C(OCH3)2CH3, the solution turns black in color. Upon completion of the reaction, UV-vis data of the resulting material indicated re-establishment of a conjugated network, and an FTIR spectrum indicated the presence of amide groups by the appearance of amide C═O stretching bands. (FIG. 11D) XRD data for graphene, graphene oxide, and allylic amide-functionalized graphene oxide is shown in FIG. 11E. XPS plots for graphene oxide, and allylic amide-functionalized graphene oxide confirmed the presence of amide functionality on the graphene surface (dialkylamides on activated carbon=399 / 9 eV). (FIGS. 11F-G) Furthermore, TGA data indicated that the functionalization was covalent in nature and that by increasing the reaction temperature, C—O functionalization decreased and C—C functionalization increased.

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Abstract

The present invention generally relates to compositions comprising and methods for forming functionalized carbon-based nanostructures.

Description

RELATED APPLICATIONS[0001]This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Application No. 61 / 409,844, filed Nov. 3, 2010, and entitled “Compositions Comprising and Methods for Forming Functionalized Carbon-Based Nanostructures” which is incorporated herein by reference in its entirety for all purposes.FIELD OF THE INVENTION[0002]The present invention generally relates to compositions comprising and methods for forming or using functionalized carbon-based nanostructures.BACKGROUND OF THE INVENTION[0003]Carbon-based nanostructures, including two-dimensional graphene nanosheets and graphene-based materials, have garnered an increasingly large amount of scientific interest in recent years due to their structural and electronic properties. Conventional methods for synthesizing graphene-based materials utilize graphite oxide (GO) as a starting material, which can be prepared in bulk quantities from commercial-grade graphite under strong oxidizing condit...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B01D53/62A24D3/16B01D15/08B01D53/74B01D53/46B01D53/56C07F5/00C07F7/28C07F1/08C07F15/00C07F15/02C07F5/06B01D53/64B01D53/14B82Y30/00C01B32/50
CPCC01B31/0213C01B31/0273C01B31/0484A24D3/163B82Y40/00H01G11/36H01M4/625Y02E60/13B82Y30/00C07D493/22C01B32/174C01B32/194C07D303/38Y02E60/10B01J31/12C07C235/40C07F1/08C07F5/00C07F5/06C07F7/28C07F15/006C07F15/02
Inventor SWAGER, TIMOTHY M.COLLINS, WILLIAM R.LEWANDOWSKI, WIKTORSCHMOIS, EZEQUIELSYDLIK, STEFANIEWALISH, JOSEPHGOODS, JOHN B.
Owner MASSACHUSETTS INST OF TECH
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