On-surface gold-catalyzed hydroamination/cyclization reaction of alkynes

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F25%3A00638867" target="_blank" >RIV/68378271:_____/25:00638867 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15640/25:73629819 RIV/68407700:21340/25:00380049
Result on the web
<a href="https://hdl.handle.net/11104/0369427" target="_blank" >https://hdl.handle.net/11104/0369427</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/D4QM00866A" target="_blank" >10.1039/D4QM00866A</a>

Result language
angličtina
Original language name
On-surface gold-catalyzed hydroamination/cyclization reaction of alkynes
Original language description
On-surface synthesis under ultra-high vacuum (UHV) conditions facilitates the fabrication of unique molecular compounds, replicating established in-solution protocols. However, the intramolecular hydroamination and cyclization (IHC) of alkynes on surfaces remain unexplored due to the challenges posed by the repulsion between the nitrogen lone pair and the alkyne π-system. Here we describe the first on-surface IHC of alkyne-functionalized molecular precursors in UHV environment on the Au(111) surface. Notably, the synthesis introduces two pyrrole groups into the quinoidal-based precursor, enabling the formation of two fused pyrrolo-benzoquinonediimine compounds not achievable in solution chemistry. To analyze the resulting reaction products, we utilized scanning tunneling microscopy and non-contact atomic force microscopy with single bond resolution, comparing these products to those obtained through traditional solution methods. In parallel to the experimental results, we provide a detailed computational description of the key role of single gold adatoms during the complete on-surface reaction.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
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OECD FORD branch
10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Project
Result was created during the realization of more than one project. More information in the Projects tab.
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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