N-Heterocyclic carbene and thiol micropatterns enable the selective deposition and transfer of copper films

She, Zhe; Narouz, Mina R.; Smith, Christene A.; MacLean, Amy G.; Loock, Hans‐Peter; Kraatz, Heinz‐Bernhard; Crudden, Cathleen M.

doi:10.1039/c9cc08919e

Cited by 26 publications

(20 citation statements)

References 24 publications

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“…While for Cu (111), the regular bare areas on the 0.6 ML sample provide enough space for reactive adsorption. We are confident that such regular structures, especially the controllable ratio of surface to volume caused by conformational switching, will be of great importance in constructing patterned supramolecular assembly carbene structures [37, 47, 48] for future applications in catalysis and beyond [8, 23] …”

Section: Discussionmentioning

confidence: 99%

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

et al. 2022

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Self‐assembly of cyclohexyl cyclic (alkyl)(amino)carbenes (cyCAAC) can be realized and reversibly switched from a close‐packed trimer phase to a chainlike dimer phase, enabled by the ring‐flip of the cyclohexyl wingtip. Multiple methods including scanning tunneling microscopy (STM), X‐ray photoelectron spectroscopy (XPS) and density functional theory (DFT) calculations identified a distinct isomer (axial or equatorial chair conformer) in each phase, and consequently support the conclusion regarding the determination of molecular surface geometry on the self‐assembly of cyCAAC. Moreover, various substrates such as Ag (111) and Cu (111) are tested to elucidate the importance of cyCAAC‐surface interactions on cyCAAC based nanopatterns. These investigations of patterned surfaces prompted a deep understanding of cyCAAC binding mode, surface geometry and reversible self‐assembly, which are of paramount significance in the areas of catalysis, biosensor design and surface functionalization.

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Section: Discussionmentioning

confidence: 99%

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

et al. 2022

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“…Bei Cu(111) hingegen bieten die regelmäßigen blanken Flächen auf der 0.6 ML Probe genügend Platz für die reaktive Adsorption. Wir sind überzeugt, dass solche regelmäßigen Strukturen, insbesondere das kontrollierbare Verhältnis von Oberfläche zu Volumen, das durch Konformationswechsel verursacht wird, von enormer Bedeutung sind, insbesondere für die Erzeugung gemusterter supramolekularer Carben‐Strukturen [37, 47, 48] zur Anwendung in der Katalyse und weit darüber hinaus [8, 23] …”

Section: Zusammenfassungunclassified

Reversible Selbstorganisation eines N‐heterocyclischen Carbens auf Metalloberflächen

et al. 2022

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Cyclohexyl(alkyl)(amino)carbene (cyCAAC) bilden selbstorganisierende Monolagen, die durch den Ring‐Flip der Cyclohexyl‐Seitengruppe reversibel von einer dicht gepackten Trimer‐Phase in eine kettenartige Dimer‐Phase umgeschaltet werden können. Mehrere Methoden, darunter Rastertunnelmikroskopie (STM), Röntgen‐Photoelektronenspektroskopie (XPS) und Dichtefunktionaltheorie (DFT)‐Berechnungen, identifizierten ein eindeutiges Isomer (axiales oder äquatoriales Sesselkonformer) in jeder Phase und stützen somit die Schlussfolgerung hinsichtlich des Einflusses der molekularen Oberflächengeometrie auf die Selbstorganisation von cyCAAC. Darüber hinaus wurden verschiedene Substrate wie Ag(111) und Cu(111) getestet, um die Bedeutung der Wechselwirkungen zwischen cyCAAC und der Oberfläche für die auf cyCAAC basierenden Nanomuster aufzuklären. Die Untersuchungen von gemusterten Oberflächen führten zu einem tieferen Verständnis der cyCAAC‐Bindungsweise, der Oberflächengeometrie und der reversiblen Selbstorganisation, die in den Bereichen Katalyse, Biosensor‐Design und Oberflächenfunktionalisierung von herausragender Bedeutung sind.

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] The ability of NHCs to produce self-assembled monolayers on a range of metallic, non-metallic, and metalloid substrates has attracted considerable interest with potential applications in multiple fields including catalysis, microelectronics, biosensing, surface protection and 3D MOF architectures. [1,2,4,10,14,[17][18][19][20][21] In such applications, it is critical to control the orientation and packing of NHC monolayers to finetune surface density, metal accessibility, and ligand orientation. Although the factors dictating binding orientation and self-assembly are not fully elucidated, several studies have pointed towards the important effect of wingtip substituents.…”

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Highly ordered N-heterocyclic carbene monolayers on Cu(111)

Angove

Grillo

Früchtl

et al. 2021

Preprint

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The benzannulated N-heterocyclic carbene, 1,3-dibenzylbenzimidazolylidene (NHCDBZ) forms large, highly ordered domains when adsorbed on a Cu(111) surface under ultrahigh vacuum conditions. A combination of scanning tunneling microscopy (STM), high resolution electron energy loss spectroscopy (HREELS) and density functional theory (DFT) calculations reveals that the overlayer consists of vertical benzannulated NHC moieties coordinating to Cu adatoms. Long range order results from the placement of the two benzyl units from a single NHC on opposite sides of the benzimidazole moiety, with the planes of their aromatic rings approximately parallel to the surface. The organization of three surface-bound benzyl substituents from three different NHCs into a triangular array controls the formation of a highly ordered Kagome-like lattice on the surface. This study illustrates the importance of dispersive interactions to control the binding geometry and self-assembly of the NHC.

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N-Heterocyclic carbene and thiol micropatterns enable the selective deposition and transfer of copper films

Abstract: Creating N-heterocyclic carbene and thiol micropatterns for electrochemical fabrication of copper micro-structures.

Cited by 26 publications

References 24 publications

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Reversible Self‐Assembly of an N‐Heterocyclic Carbene on Metal Surfaces

Reversible Selbstorganisation eines N‐heterocyclischen Carbens auf Metalloberflächen

Highly ordered N-heterocyclic carbene monolayers on Cu(111)

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