Premium
On‐Surface Formation of Cumulene by Dehalogenative Homocoupling of Alkenyl gem ‐Dibromides
Author(s) -
Sun Qiang,
Tran Bay V.,
Cai Liangliang,
Ma Honghong,
Yu Xin,
Yuan Chunxue,
Stöhr Meike,
Xu Wei
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706104
Subject(s) - cumulene , halogen , carbon fibers , halide , chemistry , atom (system on chip) , nanostructure , radical , density functional theory , carbon atom , unpaired electron , scanning tunneling microscope , photochemistry , materials science , nanotechnology , computational chemistry , organic chemistry , molecule , composite material , alkyl , composite number , computer science , embedded system
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.