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Cationic Nitrogen‐Doped Helical Nanographenes
Author(s) -
Xu Kun,
Fu Yubin,
Zhou Youjia,
Hennersdorf Felix,
Machata Peter,
Vincon Ilka,
Weigand Jan J.,
Popov Alexey A.,
Berger Reinhard,
Feng Xinliang
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707714
Subject(s) - dopant , cationic polymerization , chemistry , nitrogen , chirality (physics) , doping , materials science , crystallography , photochemistry , inorganic chemistry , organic chemistry , chiral symmetry breaking , physics , optoelectronics , quantum mechanics , nambu–jona lasinio model , quark
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.