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Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C-70 Containing Two Pentagons
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Univ Mons, Belgium.
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2016 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 27, 8364-8367 p.Article in journal (Refereed) PublishedText
Abstract [en]

Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckmin-sterfullerene C-60. In contrast, access to subunits of the homologue C-70 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 C-70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C-70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (Delta G double dagger) of 16.7 kcal mol(-1), which is further corroborated by DFT calculations.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 138, no 27, 8364-8367 p.
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Chemical Sciences
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URN: urn:nbn:se:kth:diva-190557DOI: 10.1021/jacs.6b04426ISI: 000379794400012PubMedID: 27355697OAI: oai:DiVA.org:kth-190557DiVA: diva2:952793
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QC 20160815

Available from: 2016-08-15 Created: 2016-08-12 Last updated: 2016-08-15Bibliographically approved

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Osella, Silvio
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