Functionalized Carbon-Based Nanostructures

Technology #15184

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Allylic oxygen to carbon bond transposition on graphite oxide (additional substrate oxygen groups have been removed for clarity). For the Eschenmoser–Claisen rearrangement variant, R=N(CH3)2.
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Inventors
Professor Timothy Swager
Department of Chemistry, MIT
External Link (swagergroup.mit.edu)
William Collins
Department of Chemistry, MIT
John Goods
Department of Chemistry, MIT
Wiktor Lewandowski
Department of Chemistry, MIT
Ezequiel Schmois
Department of Electrical Engineering and Computer Science, MIT
Stefanie Sydlik
David H. Koch Institute for Integrative Cancer Research, MIT
Joseph Walish
Department of Chemistry, MIT
Managed By
Jim Freedman
MIT Technology Licensing Officer - Chemicals, Instruments, Consumer Products
Patent Protection

Compositions comprising functionalized carbon-based nanostructures and related methods

US Patent Pending 2015-0336092
Publications
Claisen rearrangement of graphite oxide: a route to covalently functionalized graphenes
Angewandte Chemie, International Edition, 2011, 50: 8848–8852

Applications

Carbon-based nanostructures (such as graphene sheets or carbon nanotubes) are used in a multitude of applications, ranging from healthcare devices to solar panels. A method of increasing the range of applications for these carbon-based nanostructures is to functionalize them — where specific compounds are bonded to the nanostructure to give them certain electrical or chemical properties, or allow them to better attach to other compounds. The current technology describes methods of synthesizing a variety of functionalized carbon-based nanostructures.

Problem Addressed

While methods exist to attach functional groups to carbon nanostructures, the resulting bonds can often be very weak — unable to withstand high temperatures or harsh chemical environments. This is particularly so for functional groups added to the basal plane of the carbon nanostructure, where it is difficult to achieve covalent bonding. The current technology addresses this problem by proposing alternate compositions of functional groups that will form a stronger bond, as well as fabrication methods that will facilitate covalent bond formation.

Technology

The current technology describes various compositions of functional groups that can be strongly attached to graphene or graphene oxide, as well as methods for synthesizing these compounds. Some examples of these compositions are an allylic functional group bonded to the carbon nanostructure through a carbon-carbon bond; or the fusion of a functional group into an aromatic ring. Methods of fabricating these compositions include mixing a vapour phase sample containing the functional group with graphene or graphene oxide, and the recommendation of a catalyst when the oxidation of carbon monoxide is required for functionalization. 

Advantages

  • Enables stronger bonding of functional groups to carbon-based nanostructures
  • Provides a variety of options for functionalizing carbon-based nanostructures, to achieve different properties