Tailoring Bond Topologies in Open-Shell Graphene Nanostructures

Mishra, Shantanu; Lohr, Thorsten G.; Pignedoli, Carlo A.; Liu, Junzhi; Berger, Reinhard; Urgel, José I.; Müllen, Klaus; Feng, Xinliang; Ruffieux, Pascal; Fasel, Roman (2018). Tailoring Bond Topologies in Open-Shell Graphene Nanostructures. ACS nano, 12(12), pp. 11917-11927. American Chemical Society 10.1021/acsnano.8b07225

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Polycyclic aromatic hydrocarbons exhibit a rich spectrum of physicochemical properties depending on the size and, more critically, on the edge and bond topologies. Among them, open-shell systems—molecules hosting unpaired electron densities—represent an important class of materials for organic electronic, spintronic, and optoelectronic devices, but remain challenging to synthesize in solution. We report the on-surface synthesis and scanning tunneling microscopy- and spectroscopy-based study of two ultralow-gap open-shell molecules, namely peri-tetracene, a benzenoid graphene fragment with zigzag edge topology, and dibenzo[a,m]dicyclohepta[bcde,nopq]rubicene, a nonbenzenoid nonalternant structural isomer of peri-tetracene with two embedded azulene units. Our results provide an understanding of the ramifications of altered bond topologies at the single-molecule scale, with the prospect of designing functionalities in carbon-based nanostructures via engineering of bond topology.

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