Introducing Design Strategies to Preserve N‐Heterocycles Throughout the On‐Surface Synthesis of Graphene Nanostructures

Author:

Tenorio Maria1,Moreno Cesar12,Vilas‐Varela Manuel3,Castro‐Esteban Jesús3,Febrer Pol1,Pruneda Miguel1,Peña Diego3ORCID,Mugarza Aitor14

Affiliation:

1. Catalan Institute of Nanoscience and Nanotechnology (ICN2) CSIC and The Barcelona Institute of Science and Technology Bellaterra Barcelona 08193 Spain

2. Departamento de Ciencias de la Tierra y Física de la Materia Condensada Universidad de Cantabria Santander 39005 Spain

3. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS) Departamento de Química Orgánica Universidade de Santiago de Compostela Santiago de Compostela 15782 Spain

4. ICREA Institució Catalana de Recerca i Estudis Avançats Barcelona 08010 Spain

Abstract

AbstractDespite the impressive advances in the synthesis of atomically precise graphene nanostructures witnessed during the last decade, advancing in compositional complexity faces major challenges. The concept of introducing the desired functional groups or dopants in the molecular precursor often fails due to their lack of stability during the reaction path. Here, a study on the stability of different pyridine and pyrimidine moieties during the on‐surface synthesis of graphene nanoribbons on Au(111) is presented. Combining bond‐resolved scanning tunneling microscopy with X‐ray photoelectron spectroscopy, the thermal evolution of the nitrogen dopants throughout the whole reaction sequence is tracked. A comparative experimental and ab initio electronic characterization confirms the presence of dopants in the final structures, revealing also that the pyridinic nitrogen leads to a significant band downshift. The results demonstrate that, by using synthetic strategies to lower the reaction temperatures, one can preserve specific N‐heterocycles throughout all the reaction steps of the synthesis of graphene nanoribbons and beyond the interibbon coupling reaction that leads to nanoporous graphene.

Funder

Agencia Estatal de Investigación

European Commission

Xunta de Galicia

Barcelona Supercomputing Center

Publisher

Wiley

Subject

General Materials Science,General Chemistry

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