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†

Lin Feng,^a Tao Wang,

^a Hongxing Jia,^b Jianmin Huang,^a Dong Han,^a Wenzhao Zhang,^a Honghe Ding,^a Qian Xu,^a Pingwu Du

^b and Junfa Zhu

*^a

Author affiliations

* Corresponding authors

^a 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, China
E-mail: jfzhu@ustc.edu.cn

^b 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, P. R. China
E-mail: dupingwu@ustc.edu.cn

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.

Chemical Communications

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

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

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