期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 37, 页码 12976-12984出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04783
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资金
- German Science Foundation (DFG) [SFB 953, EXC 315, GRK 1896]
- European Research Council (ERC-StG SURFLINK) [637831]
- European Research Council (ERC) [637831] Funding Source: European Research Council (ERC)
We demonstrate the on-surface synthesis of porous carbon nanoribbons on Ag(111) via a preprogrammed isomerization of conformationally flexible polymer chains followed by dehydrogenation reactions using thermal annealing. The carbon chains are fabricated by polymerization of prochiral 1,3,5-tris(3-bromophenyl)benzene (mTBPB) directly on the surface using an Ullmann-type reaction. At room temperature, mTBPB partially self assembles in halogen-bonded 2D networks, which transform into organometallic chains and rings after debromination. The chain and ring formation is facilitated by conformational switching from a C-3h to C-s symmetry of mTBPB via rotation of m-phenylene units. The high conformational selectivity toward C-s-conformers is templated by the twofold coordination to Ag adatoms. After thermally induced covalent-linking through aryl-aryl coupling, well-ordered nanoporous chains are created. Finally, the rotation of single phenylene units in combination with dehydrogenation cross-linking reactions within the polymer chains leads to the unexpected formation of porous carbon nanoribbons. We unveil the reaction mechanism in a low-temperature scanning tunneling microscopy study and demonstrate that the rotation of m-phenylene units is a powerful design tool to promote structural control in the synthesis of cyclic covalent organic nanostructures on metal surfaces.
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