Citation
Weidner, Tobias; Zharnikov, Michael; Hoβbach, Jens; Castner, David G.; & Siemeling, Ulrich (2010).
Adamantane-Based Tripodal Thioether Ligands Functionalized with a Redox-Active Ferrocenyl Moiety for Self-Assembled Monolayers.
J Phys Chem C Nanomater Interfaces, 114(35), 14975-14982.
Abstract
Self-assembled monolayers (SAMs) can decorate surfaces with `smart´ functional units possessing reversible stimulus-response behavior for optical, thermal, magnetic or redox-chemical stimuli. An independent performance of individual functional groups in such a film is desirable, which can be, in particular, ensured by fairly large lateral separations between tailgroups in the SAM. Adsorbate molecules with multiple attachment points are very promising in this context owing to their large surface footprint, which covers a surface area exceeding the lateral dimensions of the functional groups. To address these design constraints, novel tridentate long-chain tripodal thioether ligands with central adamantine units and a redox-active ferrocenyl tailgroup, 1-[4-(ferrocenylethynyl)phenyl]-3,5,7-tri[(4-n-octylsulfanyl)phenyl]adamantine (T8) and 1-[4-(ferrocenylethynyl)phenyl]-3,5,7-tri[(4-n-dodecylsulfanyl)phenyl]adamantine (T12), were synthesized and used as tripodal adsorbate molecules for the fabrication of redox-active ferrocenyl-terminated SAMs on Au(111). These SAMs were characterized by X-ray photoelectron spectroscopy, near edge X-ray absorption fine structure spectroscopy and sum frequency generation spectroscopy. The data suggest that T8 and T12 form almost contamination-free, well-aligned and fairly densely-packed SAMs on Au(111) with laterally separated ferrocenyl units. The SAMs show a homogeneous binding chemistry, an important requirement for high fidelity SAMs. SFG results indicate lateral interactions between neighboring molecules via the long-chain binding units.
Reference Type
Journal Article
Secondary Title
J Phys Chem C Nanomater Interfaces
Author(s)
Weidner, TobiasZharnikov, MichaelHoβbach, JensCastner, David G.Siemeling, Ulrich
Year Published
2010
Date Published
1283990400
Volume Number
114
Issue Number
35
Pages
14975-14982
ISSN/ISBN
1932-7447
DOI
10.1021/jp104376p
