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On-surface synthesis of porous graphene nanoribbons containing nonplanar [14]annulene pores |
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| Authors: | M R Ajayakumar Marco Di Giovannantonio Carlo A Pignedoli Lin Yang Pascal Ruffieux Ji Ma Roman Fasel Xinliang Feng |
| Institution: | 1. Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden, Germany;2. nanotech@surfaces laboratory, Empa – Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland
Contribution: Investigation (equal), Writing - original draft (equal);3. nanotech@surfaces laboratory, Empa – Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland Contribution: Investigation (supporting);4. Center for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden, Germany Contribution: Investigation (supporting);5. nanotech@surfaces laboratory, Empa – Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland Contribution: Supervision (supporting), Writing - review & editing (supporting);6. nanotech@surfaces laboratory, Empa – Swiss Federal Laboratories for Materials Science and Technology, Dübendorf, Switzerland |
| Abstract: | The precise introduction of nonplanar pores in the backbone of graphene nanoribbon represents a great challenge. Here, we explore a synthetic strategy toward the preparation of nonplanar porous graphene nanoribbon from a predesigned dibromohexabenzotetracene monomer bearing four cove-edges. Successive thermal annealing steps of the monomers indicate that the dehalogenative aryl-aryl homocoupling yields a twisted polymer precursor on a gold surface and the subsequent cyclodehydrogenation leads to a defective porous graphene nanoribbon containing nonplanar 14]annulene pores and five-membered rings as characterized by scanning tunneling microscopy and noncontact atomic force microscopy. Although the C–C bonds producing 14]annulene pores are not achieved with high yield, our results provide new synthetic perspectives for the on-surface growth of nonplanar porous graphene nanoribbons. |
| Keywords: | cove-edge five-membered ring graphene nanoribbon nanopore nonplanar on-surface synthesis |