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Dechlorinated Ullmann Coupling Reaction of Aryl Chlorides on Ag(111): A Combined STM and XPS Study
Author(s) -
Dai Jingxin,
Zhao Wenhui,
Xing Lingbo,
Shang Jian,
Ju Huanxin,
Zhou Xiong,
Liu Jing,
Chen Qiwei,
Wang Yongfeng,
Zhu Junfa,
Wu Kai
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.201900264
Subject(s) - aryl , x ray photoelectron spectroscopy , chemistry , coupling reaction , ullmann reaction , coupling (piping) , photochemistry , computational chemistry , inorganic chemistry , catalysis , organic chemistry , materials science , chemical engineering , metallurgy , alkyl , engineering
Surface‐assisted Ullmann coupling was widely applied to construct various molecular nanostructures on surfaces due to its reliability and controllability. By using 4,4′′‐dichloro‐1,1′:3′,1′′‐terphenyl (DCTP) as the precursor, covalently bonded zig‐zag oligophenylene chains and hexagonal hyperbenzene rings, e. g., [18]‐honeycombenes, were successfully fabricated on Ag(111) via dechlorinated Ullmann coupling reaction. Stepwise annealing was applied to investigate the reaction process in detail. Scanning tunneling microscopy and synchrotron X‐ray photoemission spectroscopy were utilized to explore the thermal evolution of the DCTP molecules on Ag(111) under ultrahigh vacuum conditions, evidencing the existence of intact DCTP molecules, chemisorbed Cl atoms, covalently bonded DCTP dimers as well as organometallic C−Ag−C‐containing intermediates. These results may help understand dechlorinated Ullmann coupling reaction of aryl chlorides on metal surfaces.