On-surface synthesis of planar acenes via regioselective aryl-aryl coupling

Lin Feng; Tao Wang; Hongxing Jia; Jianmin Huang; Dong Han; Wenzhao Zhang; Honghe Ding; Qian Xu; Pingwu Du; Junfa Zhu

doi:10.1039/d0cc01043j

On-surface synthesis of planar acenes via regioselective aryl-aryl coupling

Chem Commun (Camb). 2020 May 5;56(36):4890-4893. doi: 10.1039/d0cc01043j.

Authors

Lin Feng¹, Tao Wang¹, Hongxing Jia², Jianmin Huang¹, Dong Han¹, Wenzhao Zhang¹, Honghe Ding¹, Qian Xu¹, Pingwu Du², Junfa Zhu¹

Affiliations

¹ National Synchrotron Radiation Laboratory, Department of Chemical Physics and Key Laboratory of Surface and Interface Chemistry and Energy Catalysis of Anhui Higher Education Institutes, University of Science and Technology of China, Hefei, 230029, China. jfzhu@ustc.edu.cn.
² Hefei National Laboratory of Physical Science at the Microscale, CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), University of Science and Technology of China, 96 Jinzhai Road, Hefei, 230026, P. R. China. dupingwu@ustc.edu.cn.

PMID: 32236253
DOI: 10.1039/d0cc01043j

Abstract

The reaction of 2,2'-dibromo-biphenyl on a Ag(111) surface leads to the formation of planar acenes with a high-regioselectivity rather than nonplanar saddle-shaped tetraphenylene as the typical product in solution chemistry. The regioselective aryl-aryl coupling reaction is attributed to the hydrogen repulsion between the reactants on the confined two-dimensional surface.