5 years ago

Cationic Nitrogen-Doped Helical Nanographenes

Cationic Nitrogen-Doped Helical Nanographenes
Kun Xu, Felix Hennersdorf, Alexey A. Popov, Youjia Zhou, Xinliang Feng, Reinhard Berger, Ilka Vincon, Peter Machata, Yubin Fu, Jan J. Weigand
Herein, we report the design and synthesis of a series of novel cationic nitrogen-doped nanographenes (CNDNs) with nonplanar geometry and axial chirality. Single-crystal X-ray analysis reveals helical and cove-edged structures. Compared to their all-carbon analogues, the frontier orbitals of the CNDNs are energetically lower lying, with a reduced optical energy gap and greater electron-accepting behavior. Cyclic voltammetry shows all the derivatives to undergo quasireversible reductions. In situ spectroelectrochemical studies prove that, depending on the number of nitrogen dopants, either neutral radicals (one nitrogen dopant) or radical cations (two nitrogen dopants) are formed upon reduction. The concept of cationic nitrogen doping and introducing helicity into nanographenes paves the way for the design and synthesis of expanded nanographenes or even graphene nanoribbons with cationic nitrogen dopants. Nitrogen plus: A new bottom-up synthetic method allows the generation of cationic nitrogen-doped nanographenes with nonplanar helical structures. The new nanographenes have interesting properties and have potential use as optical and electronic materials.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707714

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