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

Li, Qing; Gao, Jianzhi; Li, Youyong; Fuentes-Cabrera, Miguel; Liu, Mengxi; Qiu, Xiaohui; Lin, Haiping; Chi, Lifeng; Pan, Minghu

doi:10.1038/s41467-018-05472-2

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

Journal Article · Mon Aug 06 00:00:00 EDT 2018 · Nature Communications

DOI:https://doi.org/10.1038/s41467-018-05472-2· OSTI ID:1463979

Li, Qing ^[1]; Gao, Jianzhi ^[2];

^[1]; Fuentes-Cabrera, Miguel ^[3]; Liu, Mengxi ^[4]; Qiu, Xiaohui ^[5];

^[1]; Chi, Lifeng ^[1]; Pan, Minghu ^[6]

Soochow Univ., Suzhou (China). Inst. of Functional Nano & Soft Materials (FUNSOM). Jiangsu Key Lab. for Carbon-Based Functional Materials & Devices
Shaanxi Normal Univ., Xi’an (China). School of Physics and Information Technology
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences. Computational Sciences and Engineering Division
National Center for Nanoscience and Technology, Beijing (China). CAS Key Lab. of Standardization and Measurement for Nanotechnology. CAS Center for Excellence in Nanoscience
National Center for Nanoscience and Technology, Beijing (China). CAS Key Lab. of Standardization and Measurement for Nanotechnology. CAS Center for Excellence in Nanoscience; Univ. of Chinese Academy of Sciences, Beijing (China)
Huazhong Univ. of Science and Technology, Wuhan (China). School of Physics

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); Soochow University, Suzhou (China); National Center for Nanoscience and Technology, Beijing (China)

Sponsoring Organization:: USDOE Office of Science (SC); National Natural Science Foundation of China (NSFC); Natural Science Foundation of Jiangsu Province (China); Major State Basic Research Development Program of China

Grant/Contract Number:: AC05-00OR22725; 21622306; 91545127; 21790053; 21771134; 11574095; BK20140305; BK20150305; 2017YFA0205002; 2017YFA0204800; 2014CB932600

OSTI ID:: 1463979

Journal Information:: Nature Communications, Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 29 works

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