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- Publisher Website: 10.1021/ja074403b
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Article: Synthesis, structure, and isomerization of decapentynylcorannulene: Enediyne cyclization/lnterconversion of C40 R10 isomers
Title | Synthesis, structure, and isomerization of decapentynylcorannulene: Enediyne cyclization/lnterconversion of C<inf>40</inf>R<inf>10</inf> isomers |
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Authors | |
Issue Date | 2007 |
Citation | Journal of the American Chemical Society, 2007, v. 129, n. 42, p. 12612-12613 How to Cite? |
Abstract | Decapentynylcorannulene (5) is prepared via aryl-alkyne coupling chemistry of decachlorocorannulene and trimethylstannylpentyne. The crystal structure of 5 is compared with the ab initio computed structure of decaethynylcorannulene (3). The relative structure and energetics of 3 and its carbon nanotube isomer C40H10 (2) are discussed. Per-alkynyl-polynuclear aromatic hydrocarbons, such as 3, constitute a high energy form of carbon-rich compounds. During the synthesis of 3, enediyne cyclization forms the diradical, which ring-opens to the biscumulenyl [10]annulene (6). Discovery of this process supports the idea that derivatives of 2 could result from corresponding derivatives of 3 through electrocyclic mechanisms and demonstrates a new carbon skeletal rearrangement for strained polynuclear aromatic networks. Derivatives of 3, like 5, warrant further investigation to find viable precursors for monodispersed single-walled carbon-based nanotubes. Copyright © 2007 American Chemical Society. |
Persistent Identifier | http://hdl.handle.net/10722/341518 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Hayama, Tomoharu | - |
dc.contributor.author | Wu, Yao Ting | - |
dc.contributor.author | Linden, Anthony | - |
dc.contributor.author | Baldridge, Kim K. | - |
dc.contributor.author | Siegel, Jay S. | - |
dc.date.accessioned | 2024-03-13T08:43:26Z | - |
dc.date.available | 2024-03-13T08:43:26Z | - |
dc.date.issued | 2007 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2007, v. 129, n. 42, p. 12612-12613 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/341518 | - |
dc.description.abstract | Decapentynylcorannulene (5) is prepared via aryl-alkyne coupling chemistry of decachlorocorannulene and trimethylstannylpentyne. The crystal structure of 5 is compared with the ab initio computed structure of decaethynylcorannulene (3). The relative structure and energetics of 3 and its carbon nanotube isomer C40H10 (2) are discussed. Per-alkynyl-polynuclear aromatic hydrocarbons, such as 3, constitute a high energy form of carbon-rich compounds. During the synthesis of 3, enediyne cyclization forms the diradical, which ring-opens to the biscumulenyl [10]annulene (6). Discovery of this process supports the idea that derivatives of 2 could result from corresponding derivatives of 3 through electrocyclic mechanisms and demonstrates a new carbon skeletal rearrangement for strained polynuclear aromatic networks. Derivatives of 3, like 5, warrant further investigation to find viable precursors for monodispersed single-walled carbon-based nanotubes. Copyright © 2007 American Chemical Society. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Synthesis, structure, and isomerization of decapentynylcorannulene: Enediyne cyclization/lnterconversion of C<inf>40</inf>R<inf>10</inf> isomers | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/ja074403b | - |
dc.identifier.scopus | eid_2-s2.0-35548961925 | - |
dc.identifier.volume | 129 | - |
dc.identifier.issue | 42 | - |
dc.identifier.spage | 12612 | - |
dc.identifier.epage | 12613 | - |
dc.identifier.isi | WOS:000250327000013 | - |