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On‐Surface Synthesis of Unsaturated Hydrocarbon Chains through C−S Activation
Author(s) -
Giovanelli Luca,
Pawlak Rémy,
Hussein Fatima,
MacLean Oliver,
Rosei Federico,
Song Wentao,
Pigot Corentin,
Dumur Frédéric,
Gigmes Didier,
Ksari Younal,
Bondino Federica,
Magnano Elena,
Meyer Ernst,
Clair Sylvain
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202200809
Subject(s) - pentalene , annealing (glass) , hydrocarbon , photoemission spectroscopy , graphene , chemistry , conjugated system , photochemistry , materials science , nanotechnology , chemical engineering , molecule , x ray photoelectron spectroscopy , organic chemistry , engineering , composite material , polymer
We use an on‐surface synthesis approach to drive the homocoupling reaction of a simple dithiophenyl‐functionalized precursor on Cu(111). The C−S activation reaction is initiated at low annealing temperature and yields unsaturated hydrocarbon chains interconnected in a fully conjugated reticulated network. High‐resolution atomic force microscopy imaging reveals the opening of the thiophenyl rings and the presence of trans ‐ and cis ‐oligoacetylene chains as well as pentalene units. The chemical transformations were studied by C 1s and S 2p core level photoemission spectroscopy and supported by theoretical calculations. At higher annealing temperature, additional cyclization reactions take place, leading to the formation of small graphene flakes.