Exploring a Route to Cyclic Acenes by On‐Surface Synthesis

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-07, Vol.58 (27), p.9038-9042
Main Authors: Schulz, Fabian, García, Fátima, Kaiser, Katharina, Pérez, Dolores, Guitián, Enrique, Gross, Leo, Peña, Diego
Format: Article
Language:English
Subjects:
arynes
Atomic force microscopy
carbon nanobelts
Communication
Communications
cyclacenes
cycloadditions
Microscopy
Oxygen atoms
Reaction products
scanning tunneling microscopy
Synthesis
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Summary: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. Coming full circle: A route to obtain cyclacenes by combining solution and on‐surface chemistry is proposed. Epoxycyclacenes were prepared by a sequence of Diels–Alder cycloadditons, and they were visualized and partially deoxygenated on the Cu(111) surface by scanning probe microscopy.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201902784