Cross-coupling of aryl-bromide and porphyrin-bromide on an Au(111) surface

Guowen Kuang; Qiushi Zhang; Deng Yuan Li; Xue Song Shang; Tao Lin; Pei Nian Liu; Nian Lin

doi:10.1002/chem.201501095

Cross-coupling of aryl-bromide and porphyrin-bromide on an Au(111) surface

Chemistry. 2015 May 26;21(22):8028-32. doi: 10.1002/chem.201501095. Epub 2015 Apr 16.

Authors

Guowen Kuang¹, Qiushi Zhang¹, Deng Yuan Li², Xue Song Shang², Tao Lin¹, Pei Nian Liu³, Nian Lin⁴

Affiliations

¹ Department of Physics, The Hong Kong University of Science and Technology, Clear Water Bay (Hong Kong).
² Shanghai Key Laboratory of Functional Materials Chemistry and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai (P. R. China).
³ Shanghai Key Laboratory of Functional Materials Chemistry and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road 130, Shanghai (P. R. China). liupn@ecust.edu.cn.
⁴ Department of Physics, The Hong Kong University of Science and Technology, Clear Water Bay (Hong Kong). phnlin@ust.hk.

PMID: 25882898
DOI: 10.1002/chem.201501095

Abstract

Cross-coupling is of great importance in organic synthesis. Here it is demonstrated that cross-coupling of aryl-bromide and porphyrin-bromide takes place on a Au(111) surface in vacuo. The products are oligomers consisting of porphyrin moieties linked by p-phenylene at porphyrin's meso-positions. The ratio of the cross-coupled versus homocoupled bonds can be regulated by the reactant concentrations. Kinetic Monte Carlo simulations were applied to determine the activation barrier. It is expected that this reaction can be employed in other aryl-bromide precursors for designing alternating co-polymers incorporating porphyrin and other functional moieties.

Keywords: cross-coupling; gold; kinetic Monte Carlo simulation; scanning tunneling microscopy; surface chemistry.