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

Date:2018-10-16Keywords:Copper, RadialenesView:1178


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* & Minghu Pan* 


1Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou 215123, China. 

2School of Physics and Information Technology, Shaanxi Normal University, Xi’an 710062, China. 

3Center for Nanophase Materials Sciences, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA. 

4Computational Sciences and Engineering Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA. 

5CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190, China. 

6University of Chinese Academy of Sciences, Beijing 100049, China. 

7School of Physics, Huazhong University of Science and Technology, Wuhan 430074, China.


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.