Self-assembly directed one-step synthesis of [4]radialene on Cu(100) surfaces

Qing Li, Jianzhi Gao, Youyong Li, Miguel Fuentes-Cabrera, Mengxi Liu, Xiaohui Qiu, Haiping Lin (), Lifeng Chi () and Minghu Pan ()
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Qing Li: Soochow University
Jianzhi Gao: Shaanxi Normal University
Youyong Li: Soochow University
Miguel Fuentes-Cabrera: Oak Ridge National Laboratory
Mengxi Liu: CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology
Xiaohui Qiu: CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology
Haiping Lin: Soochow University
Lifeng Chi: Soochow University
Minghu Pan: Huazhong University of Science and Technology

Nature Communications, 2018, vol. 9, issue 1, 1-7

Abstract: Abstract The synthetic challenges of radialenes have precluded their practical applications. Here, we report a one-step synthetic protocol of [4]radialene on a copper surface. High-resolution scanning tunneling microscopy measurements reveal that such catalytic reaction proceeds readily with high selectivity at the temperature below 120 K. First-principles calculations show that the reaction pathway is characterized by firstly the cooperative inter-molecular hydrogen tautomerization and then the C–C bond formation. The feasibility of such cyclotetramerization reaction can be interpreted by the surface effect of Cu(100), which firstly plays an important role in directing the molecular assembly and then serves as an active catalyst in the hydrogen tautomerization and C–C coupling processes. This work presents not only a novel strategy to the scant number of synthetic methods to produce [4]radialenes via a novel [1 + 1 + 1 + 1] reaction pathway, but also a successful example of C–C bond coupling reactions guided by the surface-induced C–H/π assembly.

Date: 2018
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DOI: 10.1038/s41467-018-05472-2

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