ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Ring Contraction of Cyclooctatetraenes toward Non-Benzenoid Polycyclic Aromatic Hydrocarbons by Au(111)-Catalysis and Bulk Pyrolysis.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- On-Surface Synthesis of Nonbenzenoid PAHs Using Intermolecular π-Radical C-C Coupling.Journal of the American Chemical Society · 2025Article
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Authors and funding
12 authors.
Funding
Abstract
The Au(111)-catalyzed cyclodehydrogenation of tetraphenylated diacenaphtho-cyclooctatetraene (DA-COT) and tetraacenaphtho-cyclooctatetraene (TA-COT) was investigated and compared with their uncatalyzed bulk pyrolysis. On Au(111), a strain-induced contraction of the central COT unit toward six-membered rings upon extrusion of alkynes occurred. For TA-COT, an alternative reaction pathway opened up due to the increased ring strain of the eliminated alkyne product. This pathway involved a rearrangement toward a non-benzenoid polycyclic aromatic hydrocarbon containing a sesquifulvalene core. Intermediates and (by-)products were observed by high-resolution scanning tunneling microscopy (STM) and non-contact atomic force microscopy (nc-AFM), verifying the predicted reaction mechanism. Formation of [8]circulene derivatives was not observed. Uncatalyzed bulk pyrolysis only gave one ring contraction product, respectively, for both COT derivatives.
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