On-Surface Formation of Cumulene by Dehalogenative Homocoupling of Alkenyl gem-Dibromides

Qiang Sun, Bay V. Tran, Liangliang Cai, Honghong Ma, Xin Yu, Chunxue Yuan, Meike Stöhr, Wei Xu

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Abstract

The on-surface activation of carbon-halogen groups is an efficient route to produce radicals for constructing various hydrocarbons and carbon nanostructures. To date, the employed halide precursors have only one halogen attached to a carbon atom. It is thus of interest to study the effect of attaching more than one halogen atom to a carbon atom with the aim of producing multiple unpaired electrons. By introducing an alkenyl gem-dibromide, cumulene products were fabricated on a Au(111) surface by dehalogenative homocoupling reactions. The reaction products and pathways were unambiguously characterized by a combination of high-resolution scanning tunneling microscopy and non-contact atomic force microscopy measurements together with density functional calculations. This study further supplements the database of on-surface synthesis strategies and provides a facile manner for incorporation of more complicated carbon scaffolds into surface nanostructures.

Original languageEnglish
Pages (from-to)12165-12169
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number40
Early online date28-Aug-2017
DOIs
Publication statusPublished - 25-Sept-2017

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