Adsorption of 4-(N,N-Dimethylamino)-4′-nitrostilbene on an Amorphous Silica Glass Surface

Author(s): Dóra Vörös, Andrea Angeletti, Cesare Franchini, Sebastian Mai, Leticia González
Abstract: Stilbenes are a compelling class of organic photoswitches with a high degree of tunability that sensitively depend on their environment. In this study, we investigate the adsorption properties of 4-(N,N-dimethylamino)-4′-nitrostilbene (DANS), a push-pull stilbene, on amorphous silica glass. Plane-wave density functional theory (DFT) calculations are used to understand how the trans and cis isomers of DANS interact with the amorphous surface and which are the most preferred modes of adsorption. Our calculations revealed that the O-H···O hydrogen bonds between the nitro group and hydroxyl groups of the silica surface dominate the intramolecular interaction. In addition to hydrogen bonding, O-H···π interactions with the aromatic ring and double bond play a critical role in adsorption, whereas C-H···O interactions are present, but contribute little. Therefore, both isomers of DANS favor parallel orientations such that not only the functional groups but also the aromatic parts can strongly interact with the glass surface.
Organisation(s): Computational and Soft Matter Physics, Computational Materials Physics, Department of Theoretical Chemistry
External organisation(s): University of Bologna
Journal: Journal of Physical Chemistry C
Volume: 127
Pages: 22964-22974
No. of pages: 11
ISSN: 1932-7447
DOI: https://doi.org/10.1021/acs.jpcc.3c05552
Publication date: 11-2023
Peer reviewed: Yes
Austrian Fields of Science 2012: 104017 Physical chemistry, 103018 Materials physics, 104011 Materials chemistry
ASJC Scopus subject areas: Electronic, Optical and Magnetic Materials, Energy(all), Physical and Theoretical Chemistry, Surfaces, Coatings and Films
Portal url: https://ucrisportal.univie.ac.at/en/publications/adsorption-of-4nndimethylamino4nitrostilbene-on-an-amorphous-silica-glass-surface(5cb60f30-2c67-41d7-9ea1-80de82b452f3).html