Cationic Nitrogen-Doped Helical Nanographenes

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

Abstract

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.

Details

Original languageEnglish
Pages (from-to)15876-15881
Number of pages6
JournalAngewandte Chemie - International Edition
Volume56
Issue number50
Publication statusPublished - 11 Dec 2017
Peer-reviewedYes

External IDs

Scopus 85037351448
PubMed 28902969
ORCID /0000-0001-7323-7816/work/142257362

Keywords

ASJC Scopus subject areas

Keywords

  • graphene, helicene, nanographene, nitrogen doping, polycyclic aromatic hydrocarbons