On-surface synthesis of nonbenzenoid PAHs using intermolecular π-radical C-C coupling

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F25%3A00642925" target="_blank" >RIV/68378271:_____/25:00642925 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15640/25:73632759
Result on the web
<a href="https://hdl.handle.net/11104/0373436" target="_blank" >https://hdl.handle.net/11104/0373436</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jacs.5c12864" target="_blank" >10.1021/jacs.5c12864</a>

Result language
angličtina
Original language name
On-surface synthesis of nonbenzenoid PAHs using intermolecular π-radical C-C coupling
Original language description
On-surface synthesis has emerged as a new research field, ideal for designing low-dimensional carbon-based nanomaterials. One of the central problems with this synthetic approach is the understanding of reaction mechanisms, which is a key point for advancing the design of novel, highly selective reactions. The concept of π-radical-mediated reactions has been rarely considered in the context of on-surface synthesis so far. Here, we demonstrate that a π-radical-mediated reaction can provide an efficient mechanism of regioselective carbon–carbon coupling. Namely, π-radical coupling enables the dimerization of two π-expanded acenaphthene units, which facilitates the formation of complex nonbenzenoid PAHs. Our work contributes to the understanding of reaction mechanisms at the fundamental level, thus bridging the gap between in-solution radical chemistry and on-surface synthesis. We demonstrate a highly selective reaction in which the crucial C–C coupling step proceeds without direct catalytic involvement of the gold surface. This mechanistic insight suggests that π-radical coupling is a promising strategy that could be potentially expanded to inert surfaces, providing suitable π-radical activation.n
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GA23-05486S" target="_blank" >GA23-05486S: On-surface synthesis and characterization of polyradical molecules</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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