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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61989592:15640/25:73629819 RIV/68407700:21340/25:00380049

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

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

Popis výsledku anglicky

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

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Materials Chemistry Frontiers

ISSN

2052-1537

e-ISSN

2052-1537

Svazek periodika

9

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

838-846

Kód UT WoS článku

001401258200001

EID výsledku v databázi Scopus

2-s2.0-85215860201