Journal
ACS NANO
Volume 8, Issue 1, Pages 709-718Publisher
AMER CHEMICAL SOC
DOI: 10.1021/nn405370s
Keywords
scanning probe microscopy; photoelectron spectroscopy; Ullmann reaction; surface chemistry; organometallic chemistry; hyperbenzene; copper
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Funding
- National Basic Research Program of China [2010C-B923302, 2013CB834605]
- National Natural Science Foundation of China [21173200]
- Specialized Research Fund for the Doctoral Program of Higher Education of Ministry of Education [20113402110029]
- Deutsche Forschungsgemeinschaft [SFB 1083]
- Chinese Academy of Sciences [2011T2J33]
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The formation, structure, and dynamics of planar organometallic macrocycles (meta-terphenyl-Cu)(n) and zigzag-shaped one-dimensional organometallic polymers on a Cu(111) surface were studied with scanning tunneling microscopy (STM) and X-ray photoelectron spectroscopy (XPS). Vapor deposition of 4,4 ''-dibromo-meta-terphenyl (DMTP) onto Cu(111) at 300 K leads to C-Br bond scission and formation of C-Cu-C bonds, which connect neighboring meta-terphenyl fragments such that room-temperature stable macrocycles and zigzag chains are formed. The chains self-assemble to form islands, which are elongated in the direction of the chains. If DMTP is deposited onto Cu(111) held at 440 K, the island size is drastically increased (>200 x 200 nm(2)). STM sequences show the formation of ordered structures through reversible scission and reformation of the C-Cu-C bonds. The cyclic organometallic species such as the hexamer (meta-terphenyl-Cu)(6) may represent intermediates in the surface-confined Ullmann synthesis of hydrocarbon macrocycles such as the recently discovered hyperbenzene.
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