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On-surface synthesis of rigid benzenoid- and nonbenzenoid-coupled porphyrin–graphene nanoribbon hybrids

Deyerling, Joel, Pörtner, Mathias, Dordevic, Luka, Riss, Alexander, Bonifazi, Davide ORCID: https://orcid.org/0000-0001-5717-0121 and Auwärter, Willi 2022. On-surface synthesis of rigid benzenoid- and nonbenzenoid-coupled porphyrin–graphene nanoribbon hybrids. Journal of Physical Chemistry C 126 (19) , 8467–8476. 10.1021/acs.jpcc.2c00912

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Abstract

On-surface synthesis made the fabrication of extended, atomically precise π-conjugated nanostructures on solid supports possible, with graphene nanoribbons (GNRs) and porphyrin-derived oligomers standing out. To date, examples combining these two prominent material classes are scarce, even though the chemically versatile porphyrins and the atomistic details of the nanographene spacers promise an easy tunability of structural and functional properties of the resulting hybrid structures. Here, we report the on-surface synthesis of extended benzenoid- and nonbenzenoid-coupled porphyrin–graphene nanoribbon hybrids by sequential Ullmann-type and cyclodehydrogenation reactions of a tailored Zn(II) 5,15-bis(5-bromo-1-naphthyl)porphyrin (Por(BrNaph)2) precursor on Au(111) and Ag(111). Using bond-resolved noncontact atomic force microscopy (nc-AFM) and scanning tunneling microscopy (STM), we characterize the structures of reaction intermediates and products in detail and provide insight into the effects of the annealing protocol. We further demonstrate the stability and rigidity of the extended one-dimensional porphyrin–GNR oligomers by employing an STM-based manipulation procedure, which allows for spectroscopic measurement upon lifting.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 1932-7447
Last Modified: 10 Nov 2022 11:33
URI: https://orca.cardiff.ac.uk/id/eprint/150954

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