Flexible NO 2 -Functionalized N-Heterocyclic Carbene Monolayers on Au (111) Surface

The formation of flexible self-assembled monolayers (SAMs) in which an external trigger modifies the geometry of surface-anchored molecules is essential for the development of functional materials with tunable properties. In this work, it is demonstrated that NO -functionalized N-heterocyclic carben...

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Veröffentlicht in:Chemistry : a European journal 2019-11, Vol.25 (66), p.15067-15072
Hauptverfasser: Dery, Shahar, Kim, Suhong, Tomaschun, Gabriele, Haddad, David, Cossaro, Albano, Verdini, Alberto, Floreano, Luca, Klüner, Thorsten, Toste, F Dean, Gross, Elad
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container_end_page 15072
container_issue 66
container_start_page 15067
container_title Chemistry : a European journal
container_volume 25
creator Dery, Shahar
Kim, Suhong
Tomaschun, Gabriele
Haddad, David
Cossaro, Albano
Verdini, Alberto
Floreano, Luca
Klüner, Thorsten
Toste, F Dean
Gross, Elad
description The formation of flexible self-assembled monolayers (SAMs) in which an external trigger modifies the geometry of surface-anchored molecules is essential for the development of functional materials with tunable properties. In this work, it is demonstrated that NO -functionalized N-heterocyclic carbene molecules (NHCs), which were anchored on Au (111) surface, change their orientation from tilted into flat-lying position following trigger-induced reduction of their nitro groups. DFT calculations identified that the energetic driving force for reorientation was the lower steric hindrance and stronger interactions between the chemically reduced NHCs and the Au surface. The trigger-induced changes in the NHCs' anchoring geometry and chemical functionality modified the work function and the hydrophobicity of the NHC-decorated Au surface, demonstrating the impact of a chemically tunable NHC-based SAM on the properties of the metal surface.
doi_str_mv 10.1002/chem.201903434
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title Flexible NO 2 -Functionalized N-Heterocyclic Carbene Monolayers on Au (111) Surface
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