The various binding modes of carbenes, a class of widely used ligands in organic synthesis and catalysis, have been explored in terms of their electronic structure and reactivity. More recently, with the help of surface chemistry, ultrahigh vacuum (UHV), and scanning tunneling microscopy (STM), there has been a surge of interest in analyzing binding modes of highly reactive carbene species. Several attempts have been documented that describe the growth and characterization of N-Heterocyclic carbenes (NHCs) on metal surfaces, whilst there is a paucity of studies on heterogeneous binding modes and highly reactive all-carbon carbenes. Moreover, carbenes have rarely been used as building blocks in the assembly of extended materials from one-dimensional (1D) chains to two-dimensional (2D) lattices.<br/>Herein we report an on-surface synthesis of 1D metal-organic carbene chains with NHCs and difluorenoheptalenes (DH) as ligands and gold atoms as metal centers. From solution-synthesized molecular precursors, the carbene chains grow on Au(111) surface under thermal annealing in UHV. Further, low-temperature STM and scanning tunneling spectroscopy (STS) were used to investigate both the formation and chemical structure of homo-/heterogeneous binding modes in NHC-Au-NHC, DH-Au-DH, and NHC-Au-DH chains, respectively. <i>Ab initio</i> DFT calculations corroborate the electronic structures of the carbene units and the homo-/heterogeneous bonding modes. This study sheds new light on the prospective design for high-dimensional metal-organic materials based on carbene linkers.

One-dimensional metal-carbene chains with homo-/heterogeneous binding modes

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