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Single-Molecule Resolution of an Organometallic Intermediate in a Surface-Supported Ullmann Coupling Reaction

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Weihua Wang†, Xingqiang Shi‡, Shiyong Wang†, Michel A. Van Hove‡, and Nian Lin*†

Department of Physics, The Hong Kong University of Science and Technology, Hong Kong, China

Department of Physics and Materials Science, City University of Hong Kong, Hong Kong, China

J. Am. Chem. Soc., 2011, 133 (34), pp 13264–13267

DOI: 10.1021/ja204956b

Publication Date (Web): July 18, 2011

phnlin@ust.hk.

Section:

Physical Organic Chemistry

Abstract

We have studied the organometallic intermediate of a surface-supported Ullmann coupling reaction from 4, 4″-dibromo-p-terphenyl to poly(para-phenylene) by scanning tunneling microscopy/spectroscopy and density functional theory calculations. Our study reveals at a single-molecular level that the intermediate consists of biradical terphenyl (ph)₃ units that are connected by single Cu atoms through C–Cu–C bridges. Upon further increasing the temperature, the neighboring biradical (ph)₃ units are coupled by C–C bonds forming poly(para-phenylene) oligomers while the Cu atoms are released.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Multi-Zinc-Expanded Oligoacenes: An Intriguing Class of Well-Defined Open-Shell Singlet Diradicals
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The Journal of Physical Chemistry C2012 Article ASAP
- Multi-Zinc-Expanded Oligoacenes: An Intriguing Class of Well-Defined Open-Shell Singlet Diradicals
  Hongfang Yang, Qisheng Song, Wenchao Li, Xinyu Song, and Yuxiang Bu
  The Journal of Physical Chemistry C2012 Article ASAP
  Two classes of multi-Zn-expanded oligoacenes from benzene to pentacene are computationally designed through introducing a Zn array into acene rings in two ways: acene-chain axial versus single-ring quasi-transversal direction. Combined density functional ...
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