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Kinetically Controlled Synthesis of Four‐ and Six‐Member Cyclic Products via Sequential Aryl‐Aryl Coupling on a Au(111) Surface
Author(s) -
Zhang Ran,
Xia Bowen,
Xu Hu,
Lin Nian
Publication year - 2019
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201900256
Subject(s) - aryl , chemistry , scanning tunneling microscope , molecule , coupling reaction , kinetics , density functional theory , reaction mechanism , computational chemistry , combinatorial chemistry , photochemistry , crystallography , nanotechnology , materials science , organic chemistry , catalysis , alkyl , physics , quantum mechanics
We synthesize four‐ and six‐member cyclic products via sequential multi‐step aryl‐aryl coupling reactions of 2,3,6,7,10,11‐hexabromotriphenylene molecules on a Au(111) surface. The final products as well as the organo‐gold intermediate structures are identified using scanning tunneling microscopy and density‐functional theory simulation. By adjusting reaction temperature and post‐annealing temperature, we enhance/suppress the yields of the four‐member and six‐member cyclic products. We propose an underlying mechanism which is associated with different reaction kinetics of the first‐order and second‐order reactions. This work exemplifies intricate kinetically‐controlled on‐surface synthesis when multiple reactions of different reaction order are involved.