On-surface synthesis of nitrogen-doped nanographene with an [18]annulene pore on Ag(111)

Kewei Sun; Donglin Li; Takahito Kaihara; Satoshi Minakata; Youhei Takeda; Shigeki Kawai

Article On-surface synthesis of nitrogen-doped nanographene with an [18]annulene pore on Ag(111)

Kewei Sun (National Institute for Materials Science) ; Donglin Li (National Institute for Materials Science) ; Takahito Kaihara (Osaka University) ; Satoshi Minakata (Osaka University) ; Youhei Takeda (Osaka University) ; Shigeki Kawai (National Institute for Materials Science)

20231020 Com Chem s42004-023-01023-z.pdf

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Kewei Sun, Donglin Li, Takahito Kaihara, Satoshi Minakata, Youhei Takeda, Shigeki Kawai. On-surface synthesis of nitrogen-doped nanographene with an [18]annulene pore on Ag(111). Communications Chemistry. 2023, 6 (), 228.

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On-surface synthesis is of importance to fabricate low dimensional carbon-based nanomaterials with atomic precision. Here, we synthesize nitrogen-doped nanographene with an [18]annulene pore and its dimer through sequential reactions of debromination, aryl–aryl coupling, cyclodehydrogenation and C–N coupling on Ag(111) from 3,12-dibromo-7,8-diaza[5]helicene. The inner structures of the products were characterized with scanning tunneling microscopy with a CO terminated tip at low temperature. Furthermore, the first four unoccupied electronic states of the nanographene were investigated with a combination of scanning tunneling spectroscopy and theoretical calculations. Except for the LUMO + 2 state observed at +1.3 V, the electronic states at 500 mV, 750 mV and 1.9 V were attributed to the superatom molecular orbitals at the [18]annulene pore, which were significantly shifted towards the Fermi level due to the hybridization with the confined surface state.

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