Journal
ACS NANO
Volume 10, Issue 7, Pages 7023-7030Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsnano.6b03048
Keywords
acetylenic scaffolding; on-surface synthesis; scanning tunneling microscopy; C-C homocoupling surface chemistry
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Funding
- National Natural Science Foundation of China [21473123, 51403157]
- Research Fund for the Doctoral Program of Higher Education of China [20120072110045]
- Fundamental Research Funds for the Central Universities [2014KJ061]
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On-surface C-C coupling reactions of molecular precursors with alkynyl functional groups demonstrate great potential for the controllable fabrication of low-dimensional carbon nanostructures/nanomaterials, such as carbyne, graphyne, and graphdiyne, which demand the incorporation of highly active sp-hybridized carbons. Recently, through a dehydrogenative homocoupling reaction of alkynes, the possibility was presented to fabricate surface nanostructures involving acetylenic linkages, while problems lie in the fact that different byproducts are inevitably formed when triggering the reactions at elevated temperatures. In this work, by delicately designing the molecular precursors with terminal alkynyl bromide, we introduce the dehalogenative homocoupling reactions on the surface. As a result, we successfully achieve the formation of dimer structures, one-dimensional molecular wires and two-dimensional molecular networks with acetylenic scaffoldings on an inert Au(111) surface, where the unexpected C-Au-C organometallic intermediates are also observed. This study further supplements the database of on-surface dehalogenative C-C coupling reactions, and more importantly, it provides us an alternative efficient way for incorporating the acetylenic scaffolding into low-dimensional surface nanostructures.
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