Selective activation of four quasi-equivalent C–H bonds yields N-doped graphene nanoribbons with partial corannulene motifs

Yixuan Gao, Li Huang, Yun Cao, Marcus Richter, Jing Qi, Qi Zheng, Huan Yang, Ji Ma, Xiao Chang, Xiaoshuai Fu, Carlos-Andres Palma, Hongliang Lu, Yu-Yang Zhang, Zhihai Cheng, Xiao Lin, Min Ouyang, Xinliang Feng (), Shixuan Du () and Hong-Jun Gao ()
Additional contact information
Yixuan Gao: Chinese Academy of Sciences
Li Huang: Chinese Academy of Sciences
Yun Cao: Chinese Academy of Sciences
Marcus Richter: Technische Universität Dresden
Jing Qi: Chinese Academy of Sciences
Qi Zheng: Chinese Academy of Sciences
Huan Yang: Chinese Academy of Sciences
Ji Ma: Technische Universität Dresden
Xiao Chang: Chinese Academy of Sciences
Xiaoshuai Fu: Chinese Academy of Sciences
Carlos-Andres Palma: Chinese Academy of Sciences
Hongliang Lu: Chinese Academy of Sciences
Yu-Yang Zhang: Chinese Academy of Sciences
Zhihai Cheng: Renmin University of China
Xiao Lin: Chinese Academy of Sciences
Min Ouyang: University of Maryland
Xinliang Feng: Technische Universität Dresden
Shixuan Du: Chinese Academy of Sciences
Hong-Jun Gao: Chinese Academy of Sciences

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-33898-2

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