A C216-Nanographene Molecule with Defined Cavity as Extended Coronoid

• DOI: 10.1021/jacs.6b01181
• Publication Date: 2016-03-15T18:41:34Z
• Authors: Uliana Beser; Marcel Kastler; Ali Maghsoumi; Manfred Wagner; Chiara Castiglioni; Matteo Tommasini; Akimitsu Narita; Xinliang Feng; Klaus Müllen
• Keywords: Chemistry (all); Catalysis; Biochemistry; Colloid and Surface Chemistry; 01 natural sciences; 0104 chemical sciences

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.