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Exploring a Route to Cyclic Acenes by On‐Surface Synthesis
Author(s) -
Schulz Fabian,
García Fátima,
Kaiser Katharina,
Pérez Dolores,
Guitián Enrique,
Gross Leo,
Peña Diego
Publication year - 2019
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.201902784
Subject(s) - scanning tunneling microscope , molecule , characterization (materials science) , chemistry , atomic force microscopy , nanotechnology , atom (system on chip) , oxygen atom , crystallography , chemical physics , materials science , organic chemistry , computer science , embedded system
A route to generate cyclacenes by on‐surface synthesis is explored. We started by synthesizing two tetraepoxycyclacenes by sequences of Diels–Alder cycloadditions. Subsequently, these molecules were deposited onto Cu(111) and scanning‐tunneling‐microscopy(STM)‐based atom manipulation was employed to dissociate the oxygen atoms. Atomic force microscopy (AFM) with CO‐functionalized tips enabled the detailed characterization of the reaction products and revealed that, at most, two oxygens per molecule could be removed. Importantly, our experimental results suggest that the generation of cyclacenes by the described route might be possible for larger epoxycyclacenes.