Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts
Covalent functionalization significantly enhances the utility of carbon nanomaterials for many applications. Herein, we report an efficient method for the covalent functionalization of carbon nanotubes (CNTs) and graphite. This reaction involves the reduction of carbon nanomaterials with sodium naph...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2018
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| Online Access: | http://hdl.handle.net/1721.1/114438 https://orcid.org/0000-0002-0588-9545 |
| _version_ | 1826201615094251520 |
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| author | He, Maggie Swager, Timothy M |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry He, Maggie Swager, Timothy M |
| author_sort | He, Maggie |
| collection | MIT |
| description | Covalent functionalization significantly enhances the utility of carbon nanomaterials for many applications. Herein, we report an efficient method for the covalent functionalization of carbon nanotubes (CNTs) and graphite. This reaction involves the reduction of carbon nanomaterials with sodium naphthalide, followed by the addition of diaryliodonium salts. CNTs, including single-walled, double-walled, and multi-walled variants (SWCNTs, DWCNTs, and MWCNTs, respectively), as well as graphite, can be efficiently functionalized with substituted arene and heteroarene iodonium salts. The preferential transfer of phenyl groups containing electron-withdrawing groups was demonstrated by reactions with unsymmetrical iodonium salts. The lower reactivity of iodonium salts, relative to the more commonly used diazonium ions, presents opportunities for greater diversity in the selective functionalization of carbon nanomaterials. |
| first_indexed | 2024-09-23T11:54:26Z |
| format | Article |
| id | mit-1721.1/114438 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T11:54:26Z |
| publishDate | 2018 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1144382022-09-27T22:45:35Z Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts He, Maggie Swager, Timothy M Massachusetts Institute of Technology. Department of Chemistry Swager, Timothy M He, Maggie Swager, Timothy M Covalent functionalization significantly enhances the utility of carbon nanomaterials for many applications. Herein, we report an efficient method for the covalent functionalization of carbon nanotubes (CNTs) and graphite. This reaction involves the reduction of carbon nanomaterials with sodium naphthalide, followed by the addition of diaryliodonium salts. CNTs, including single-walled, double-walled, and multi-walled variants (SWCNTs, DWCNTs, and MWCNTs, respectively), as well as graphite, can be efficiently functionalized with substituted arene and heteroarene iodonium salts. The preferential transfer of phenyl groups containing electron-withdrawing groups was demonstrated by reactions with unsymmetrical iodonium salts. The lower reactivity of iodonium salts, relative to the more commonly used diazonium ions, presents opportunities for greater diversity in the selective functionalization of carbon nanomaterials. National Science Foundation (U.S.) (DMR-1410718) Swiss National Science Foundation (Early Postdoctoral Mobility Fellowship) 2018-03-29T14:02:09Z 2018-03-29T14:02:09Z 2016-12 2016-07 Article http://purl.org/eprint/type/JournalArticle 0897-4756 1520-5002 http://hdl.handle.net/1721.1/114438 He, Maggie, and Timothy M. Swager. “Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts.” Chemistry of Materials, vol. 28, no. 23, Dec. 2016, pp. 8542–49. https://orcid.org/0000-0002-0588-9545 en_US http://dx.doi.org/10.1021/acs.chemmater.6b03078 Chemistry of Materials Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Swager via Erja Kajosalo |
| spellingShingle | He, Maggie Swager, Timothy M Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title | Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title_full | Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title_fullStr | Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title_full_unstemmed | Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title_short | Covalent Functionalization of Carbon Nanomaterials with Iodonium Salts |
| title_sort | covalent functionalization of carbon nanomaterials with iodonium salts |
| url | http://hdl.handle.net/1721.1/114438 https://orcid.org/0000-0002-0588-9545 |
| work_keys_str_mv | AT hemaggie covalentfunctionalizationofcarbonnanomaterialswithiodoniumsalts AT swagertimothym covalentfunctionalizationofcarbonnanomaterialswithiodoniumsalts |