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

Liu J, Osella S, Ma J, Berger R, Beljonne D, Schollmeyer D, Feng X, Muellen K (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 138

Pages Range: 8364-8367

Journal Issue: 27

DOI: 10.1021/jacs.6b04426

Abstract

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.

Involved external institutions

Technische Universität Dresden DE Germany (DE) University of Mons / Université de Mons BE Belgium (BE) Johannes Gutenberg-Universität Mainz (JGU) DE Germany (DE) Max-Planck-Institut für Polymerforschung (MPI-P) / Max Planck Institute for Polymer Research DE Germany (DE)

How to cite

APA:

Liu, J., Osella, S., Ma, J., Berger, R., Beljonne, D., Schollmeyer, D.,... Muellen, K. (2016). Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons. Journal of the American Chemical Society, 138(27), 8364-8367. https://doi.org/10.1021/jacs.6b04426

MLA:

Liu, Junzhi, et al. "Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons." Journal of the American Chemical Society 138.27 (2016): 8364-8367.

BibTeX: Download