Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface
Abstract
Abstract 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 2 ‐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.
- Authors:
-
[1]
- Institute of Chemistry and The Center for Nanoscience and Nanotechnology Hebrew University of Jerusalem Jerusalem Israel
- Department of Chemistry University of California Berkeley California 94720 USA
- Department of Chemistry Carl von Ossietzky University Oldenburg 26111 Oldenburg Germany
- CNR-IOM Laboratorio Nazionale TASC Basovizza SS-14 Trieste 34012 Italy
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1570478
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Name: Chemistry - A European Journal Journal Volume: 25 Journal Issue: 66; Journal ID: ISSN 0947-6539
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Dery, Shahar, Kim, Suhong, Tomaschun, Gabriele, Haddad, David, Cossaro, Albano, Verdini, Alberto, Floreano, Luca, Klüner, Thorsten, Toste, F. Dean, and Gross, Elad. Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface. Germany: N. p., 2019.
Web. doi:10.1002/chem.201903434.
Dery, Shahar, Kim, Suhong, Tomaschun, Gabriele, Haddad, David, Cossaro, Albano, Verdini, Alberto, Floreano, Luca, Klüner, Thorsten, Toste, F. Dean, & Gross, Elad. Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface. Germany. https://doi.org/10.1002/chem.201903434
Dery, Shahar, Kim, Suhong, Tomaschun, Gabriele, Haddad, David, Cossaro, Albano, Verdini, Alberto, Floreano, Luca, Klüner, Thorsten, Toste, F. Dean, and Gross, Elad. Tue .
"Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface". Germany. https://doi.org/10.1002/chem.201903434.
@article{osti_1570478,
title = {Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface},
author = {Dery, Shahar and Kim, Suhong and Tomaschun, Gabriele and Haddad, David and Cossaro, Albano and Verdini, Alberto and Floreano, Luca and Klüner, Thorsten and Toste, F. Dean and Gross, Elad},
abstractNote = {Abstract 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 2 ‐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 = {10.1002/chem.201903434},
journal = {Chemistry - A European Journal},
number = 66,
volume = 25,
place = {Germany},
year = {Tue Oct 15 00:00:00 EDT 2019},
month = {Tue Oct 15 00:00:00 EDT 2019}
}
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