Selective activation of four quasi-equivalent C–H bonds yields N-doped graphene nanoribbons with partial corannulene motifs
Year: 2022
Type: article
Abstract: Selective C–H bond activation is one of the most challenging topics for organic reactions. The difficulties arise not only from the high C–H bond dissociation enthalpies but also the existence of multiple equivalent/quasi-equivalent reaction sites in organic molecules. Here, we successfully achieve the selective activation of four quasi-equivalent C–H bonds in a specially designed nitrogen-containing polycyclic hydrocarbon (N-PH). Density functional theory calculations reveal that the adsorption of N-PH on Ag(100) differentiates the activity of the four ortho C(sp3) atoms in the N-heterocycles into two groups, suggesting a selective dehydrogenation, which is demonstrated by sequential-annealing experiments of N-PH/Ag(100). Further annealing leads to the formation of N-doped graphene nanoribbons with partial corannulene motifs, realized by the C–H bond activation process. Our work provides a route of designing precursor molecules with ortho C(sp3) atom in an N-heterocycle to realize surface-induced selective dehydrogenation in quasi-equivalent sites.
Source: Nature Communications
Institutions: Chinese Academy of Sciences, Institute of Physics, University of Chinese Academy of Sciences, Center for Advancing Electronics Dresden, Technische Universität Dresden, Renmin University of China, University of Maryland, College Park, Max Planck Institute of Microstructure Physics, Songshan Lake Materials Laboratory
Language: English
Subfield: Biomedical Engineering
Field: Engineering
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $5,890
Funders: Deutsche Forschungsgemeinschaft, National Natural Science Foundation of China, Chinese Academy of Sciences, Renmin University of China, K. C. Wong Education Foundation, National Key Research and Development Program of China, Fundamental Research Funds for the Central Universities, National Supercomputing Center of Tianjin, National Supercomputing Center, Korea Institute of Science and Technology Information
Awards: G1497365792, G1657334739, G178923758, G1982078386, G3120675284, G3368773568, G3600810763, G3651033660, G3713973421, G3842906764, G389969255, Erkundung von Heteroaromatischen und antiaromatischen atompräzisen Nanographenen, G5397464714, G5620065147, G6233979915, G6432943043, G6952322517, G7885286209, G819753586, G8771983098
OpenAlex ID: W4306643155