Visualizing stepwise evolution of carbon hybridization from sp3 to sp2 and to sp

Wei Xiong, Guang Zhang, Bao De-Liang, Jianchen Lu (), Lei Gao, Yusen Li, Hui Zhang, Zilin Ruan, Zhenliang Hao, Hong-Jun Gao, Long Chen () and Jinming Cai ()
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Wei Xiong: Kunming University of Science and Technology
Guang Zhang: Tianjin University
Bao De-Liang: Vanderbilt University
Jianchen Lu: Kunming University of Science and Technology
Lei Gao: Kunming University of Science and Technology
Yusen Li: Tianjin University
Hui Zhang: Kunming University of Science and Technology
Zilin Ruan: Kunming University of Science and Technology
Zhenliang Hao: Kunming University of Science and Technology
Hong-Jun Gao: Institute of Physics & University of Chinese Academy of Sciences
Long Chen: Tianjin University
Jinming Cai: Kunming University of Science and Technology

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract Regulating carbon hybridization states lies at the heart of engineering carbon materials with tailored properties but orchestrating the sequential transition across three states has remained elusive. Here, we visiualize stepwise evolution in carbon hybridizations from sp³ to sp² and to sp states via dehydrogenation and elimination reactions of methylcyano-functionalized molecules on surfaces. Utilizing scanning probing microscopy, we distinguish three distinct carbon-carbon bond types within polymers induced by annealing at elevated temperatures. Density-functional-theory calculations unveil the pivotal role of the electron-withdrawing cyano group in activating neighboring methylene to form C(sp3)–C(sp3) bonds, and in facilitating subsequent stepwise HCN eliminations to realize the transformation across three carbon-carbon bond types. We also demonstrate the applicability of this strategy on one-dimensional molecular wires and two-dimensional covalent organic framework on different substrates. Our work expands the scope of carbon hybridization evolution and serves as an advance in flexibly engineering carbon-material by employing cyanomethyl-substituted molecules.

Date: 2025
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DOI: 10.1038/s41467-024-55719-4

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