Premium
Flexible NO 2 ‐Functionalized N‐Heterocyclic Carbene Monolayers on Au (111) Surface
Author(s) -
Dery Shahar,
Kim Suhong,
Tomaschun Gabriele,
Haddad David,
Cossaro Albano,
Verdini Alberto,
Floreano Luca,
Klüner Thorsten,
Toste F. Dean,
Gross Elad
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903434
Subject(s) - monolayer , steric effects , carbene , molecule , self assembled monolayer , chemistry , materials science , nitro , work function , density functional theory , crystallography , metal , chemical physics , nanotechnology , stereochemistry , computational chemistry , catalysis , organic chemistry , alkyl
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.