6533b7cffe1ef96bd1259a7d
RESEARCH PRODUCT
Fused Dibenzo[ a , m ]rubicene: A New Bowl-Shaped Subunit of C 70 Containing Two Pentagons
Klaus MüllenXinliang FengSilvio OsellaDieter SchollmeyerJi MaDavid BeljonneReinhard BergerJunzhi Liusubject
Fullerene010405 organic chemistryStereochemistryProtein subunitGeneral Chemistry010402 general chemistry01 natural sciencesBiochemistryCatalysis0104 chemical sciencesHigher fullereneschemistry.chemical_compoundColloid and Surface ChemistryBuckminsterfullerenechemistrydescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-01 | Journal of the American Chemical Society |