Gas‐Phase Transformation of Fluorinated Benzoporphyrins to Porphyrin‐Embedded Conical Nanocarbons
Dominik Lungerich, Jakob F. Hitzenberger, Michael Ruppel, Tibor Döpper, Matthias Witt, Ivana Ivanović‐Burmazović, Andreas Görling, Norbert Jux, Thomas Drewello
Abstract
Geodesic nitrogen-containing graphene fragments are interesting candidates for various material applications, but the available synthetic protocols, which need to overcome intrinsic strain energy during the formation of the bowl-shaped skeletons, are often incompatible with heteroatom-embedded structures. Through this mass spectrometry-based gas-phase study, we show by means of collision-induced dissociation experiments and supported by density functional theory calculations, the first evidence for the formation of a porphyrin-embedded conical nanocarbon. The influences of metalation and functionalization of the used tetrabenzoporphyrins have been investigated, which revealed different cyclization efficiencies, different ionization possibilities, and a variation of the dissociation pathway. Our results suggest a stepwise process for HF elimination from the fjord region, which supports a selective pathway towards bent nitrogen-containing graphene fragments.