Steering On-Surface Reactions by a Self-Assembly Approach

Qiwei Chen; Jacob R Cramer; Jing Liu; Xin Jin; Peilin Liao; Xiang Shao; Kurt V Gothelf; Kai Wu

doi:10.1002/anie.201700745

Steering On-Surface Reactions by a Self-Assembly Approach

Angew Chem Int Ed Engl. 2017 Apr 24;56(18):5026-5030. doi: 10.1002/anie.201700745. Epub 2017 Mar 24.

Authors

Qiwei Chen¹, Jacob R Cramer², Jing Liu¹, Xin Jin¹, Peilin Liao³, Xiang Shao⁴, Kurt V Gothelf², Kai Wu¹

Affiliations

¹ BNLMS, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
² Danish-Chinese Centre for Self-Assembly and Function of Molecular Nanostructures on Surfaces at iNANO and Department of Chemistry, Aarhus University, Aarhus C, 8000, Denmark.
³ School of Materials Engineering, Purdue University, West Lafayette, IN, 47907, USA.
⁴ Department of Chemical Physics, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei, 230026, China.

PMID: 28338262
DOI: 10.1002/anie.201700745

Abstract

4,4'-Bis(2,6-difluoropyridin-4-yl)-1,1':4',1''-terphenyl (BDFPTP) molecules underwent dehydrocyclization and covalent coupling reactions on Au(111) according to scanning tunneling microscopy (STM) measurements and density functional theory (DFT) calculations. Self-assembly of the reactants in well-defined molecular domains prior to reaction could greatly enhance the regioselectivity of the dehydrocyclization reaction and suppress defluorinated coupling, demonstrating that self-assembly can efficiently steer on-surface reactions. Such a strategy could be of great importance in surface chemistry and widely applied to control on-surface reactions.

Keywords: dehydrocyclization; density functional theory; on-surface reaction; scanning tunneling microscope; self-assembly.

Publication types

Research Support, Non-U.S. Gov't