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. 2016 Apr 6;138(13):4322-5.
doi: 10.1021/jacs.6b01181. Epub 2016 Mar 23.

A C216-Nanographene Molecule with Defined Cavity as Extended Coronoid

Uliana Beser  1 , Marcel Kastler  1 , Ali Maghsoumi  2 , Manfred Wagner  1 , Chiara Castiglioni  2 , Matteo Tommasini  2 , Akimitsu Narita  1 , Xinliang Feng  3 , Klaus Müllen  1
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A C216-Nanographene Molecule with Defined Cavity as Extended Coronoid

Uliana Beser et al. J Am Chem Soc. .

Abstract

We describe the first coronoid nanographene C216-molecule. As an extended polycyclic aromatic hydrocarbon containing a defined cavity, our molecule can be seen as a model system to study the influence of holes on the physical and chemical properties of graphene. Along the pathway of an eight-step synthesis including Yamamoto-type cyclization followed by 6-fold Diels-Alder cycloaddition, C216 was obtained by oxidative cyclodehydrogenation in the final step. The defined molecular structure with a cavity was unambiguously validated by MALDI-TOF mass spectrometry and FTIR, Raman, and UV-vis absorption spectroscopy coupled with DFT simulations.

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