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Article: Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons

TitleFused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons
Authors
Issue Date2016
Citation
Journal of the American Chemical Society, 2016, v. 138, n. 27, p. 8364-8367 How to Cite?
Abstract© 2016 American Chemical Society. Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckminsterfullerene C60. In contrast, access to subunits of the homologue C70 remains challenging. Here, we demonstrate an efficient bottom-up strategy toward a novel bowl-shaped polycyclic aromatic hydrocarbons (PAH) C34 with two pentagons. This PAH represents a subunit for C70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (ΔG‡) of 16.7 kcal mol-1, which is further corroborated by DFT calculations.
Persistent Identifierhttp://hdl.handle.net/10722/276758
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, Junzhi-
dc.contributor.authorOsella, Silvio-
dc.contributor.authorMa, Ji-
dc.contributor.authorBerger, Reinhard-
dc.contributor.authorBeljonne, David-
dc.contributor.authorSchollmeyer, Dieter-
dc.contributor.authorFeng, Xinliang-
dc.contributor.authorMüllen, Klaus-
dc.date.accessioned2019-09-18T08:34:34Z-
dc.date.available2019-09-18T08:34:34Z-
dc.date.issued2016-
dc.identifier.citationJournal of the American Chemical Society, 2016, v. 138, n. 27, p. 8364-8367-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/276758-
dc.description.abstract© 2016 American Chemical Society. Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckminsterfullerene C60. In contrast, access to subunits of the homologue C70 remains challenging. Here, we demonstrate an efficient bottom-up strategy toward a novel bowl-shaped polycyclic aromatic hydrocarbons (PAH) C34 with two pentagons. This PAH represents a subunit for C70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (ΔG‡) of 16.7 kcal mol-1, which is further corroborated by DFT calculations.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleFused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jacs.6b04426-
dc.identifier.scopuseid_2-s2.0-84979059292-
dc.identifier.volume138-
dc.identifier.issue27-
dc.identifier.spage8364-
dc.identifier.epage8367-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000379794400012-
dc.identifier.issnl0002-7863-

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