Head-to-Tail Oligomerization by Silylene-Tethered Sonogashira Coupling on Ag(111)

Sun, Kewei and Sagisaka, Keisuke and Peng, Lifen and Watanabe, Hikaru and Xu, Feng and Pawlak, Rémy and Meyer, Ernst and Okuda, Yasuhiro and Orita, Akihiro and Kawai, Shigeki. (2021) Head-to-Tail Oligomerization by Silylene-Tethered Sonogashira Coupling on Ag(111). Angewandte Chemie International Edition, 60 (36). pp. 19598-19603.

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Official URL: https://edoc.unibas.ch/86794/

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On-surface synthesis is a powerful method for the fabrication of π-conjugated nanomaterials. Herein, we demonstrate chemoselective Sonogashira coupling between (trimethylsilyl)ethynyl and chlorophenyl groups in silylethynyl- and chloro-substituted partially fluorinated phenylene ethynylenes (SiCPFPEs) on Ag(111). The desilylative Sonogashira coupling occurred with high chemoselectivity up to 75 %, while the competing Ullmann and desilylative Glaser homocoupling reactions were suppressed. A combination of bond-resolved scanning tunneling microscopy/atomic force microscopy (STM/AFM) and DFT calculations revealed that the oligomers were obtained by the formation of intermolecular silylene tethers (-Me; 2; Si-) through CH; 3; -Si bond activation at 130 °C and subsequent elimination of the tethers at an elevated temperature of 200 °C.
Faculties and Departments:05 Faculty of Science > Departement Physik > Physik > Nanomechanik (Meyer)
UniBasel Contributors:Meyer, Ernst and Pawlak, Rémy
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:11 Apr 2022 15:27
Deposited On:11 Apr 2022 15:27

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