Self-Assembly of C₆₀ π-Extended Tetrathiafulvalene (exTTF) Dyads on Gold Surfaces

Abstract

The first self-assembly of a C60 pi-extended tetrathiafulvalene (exTTF) dyad on a gold surface is reported. Four fullerene derivatives, two of them containing p-quinonoid pi-extended tetrathiafulvalenes (exTTFs), have been synthesized, and their solution electrochemistry has been investigated by means of cyclic voltammetry. Fullerene-containing SAMs of thioctic acid derivatives 3 and 6 have also been investigated by cyclic voltammetry. The cyclic voltammograms of both compounds exhibit three reversible reduction waves, and for compound 6, one irreversible oxidation process corresponding to the oxidation of the exTTF subunit is observed. Stable self-assembled monolayers (SAMs) of fullerene derivative 3 were formed on gold surfaces, whereas dyad 6 does not present a very clear electrochemical response, most probably as a result of structural rearrangements on the monolayer or charge transfer between the C60 and exTTF moieties.

Surface‐Confined Heterometallic Molecular Dyads: Merging the Optical and Electronic Properties of Fe, Ru, and Os Terpyridyl Complexes

“…Reduction potential corresponds to subsequent erasing the stored charge and return to the initial state. Notably, the charge‐retention time of the system can be tuned by inserting a barrier between the redox center/centers and the substrate 23. In the given case, the presence of the short aliphatic coupling layer increases the charge‐retention time and thereby creates a current gap between the oxidized and reduced species in the system.…”

Fullerene Substitution of Donor/Acceptor Branched Disubstituted Polyacetylenes: Significantly Accelerated Polymerization by the C60 Pendant

“…The monosubstituted acetylenic monomer 3 was first synthesized from the commercially available monomer 1, and then react with C 60 and sarcosine by a Prato reaction, [14][15][16] affording the C 60 -substituted momoner 4. The disubstituted acetylenic monomer 4 was then subject to the polymerization reaction for an appropriate reaction time with the existence of the catalyst WCl 6 -Ph 4 Sn (or MoCl 5 -Ph 4 Sn) resulting in the successful formation of the D/A disubstituted PAs PA-C 60 , as confirmed by GPC measurements; the dependence of the polymerization reaction on the reaction time is discussed in the next section.…”

Combining Molecular Spintronics with Electron Paramagnetic Resonance: The Path Towards Single-Molecule Pulsed Spin Spectroscopy

“…Furthermore, control over the lifetime has been achieved using microwave -pulses, allowing change of molecular spintronic properties by physical means [233]. To control the properties electronically, D-B-A systems can be functionalized with surface-binding groups [234][235][236][237], where basically developed techniques for functionalizing SMMs could be adapted and be used for logic gates [238]. The design of new D-B-A systems is enabled by a plethora of molecular bricks, which are reviewed elsewhere [210,[239][240][241][242][243][244][245].…”