Adsorption of a dihydro-TTF derivative on Au(111) via a thiolate complex bonding to gold adatoms

Abstract

A dihydro-TTF derivative with four acetyl-protected thiol ligands was synthesised and adsorbed on Au(111) under UHV conditions. Scanning Tunnelling Microscopy (STM) and Infrared (IR) spectroscopy show that self-organised structures are formed following annealing to 333 K, with each pair of bidentate thiolate ligands bonding to a single gold adatom in a S-Auad-S complex. Due to the lack of a direct orbital overlap between the dihydro-TTF moieties and the surface, relatively little charge transfer between TAT-TTF and the gold surface occurs.

Sulfur-driven switching of the Ullmann coupling on Au(111)

“…S2. Secondly, on the terraces the herringbone reconstruction is completely lifted after the H2S exposure [33][34][35] . We attribute the protrusions to Au adatoms originating from the lifting of the herringbone, which are decorated with S to form S-Au complex 30,[36][37][38][39][40] .…”

Synthesis of Electro-active Compounds Suitable for Adsorption on Metal Surfaces

“…A further recent illustration of the use of these methods is the synthesis of the tetrakis(acetylthio)bis(dihydro-TTF) 50 (Scheme 12). 32 This uses the same methods as shown in Scheme 10 to reduce the tetraester 48 to the tetraol 49 and condense this with thioacetic acid to give the product which was adsorbed on gold with spontaneous loss of the S-acetyl groups.…”

Regioselective bromination of 1,4-dimethoxy-2,3-dimethylbenzene and conversion into sulfur-functionalised benzoquinones

“…In connection with our ongoing studies on electroactive compounds adsorbed onto metal surfaces, 1 we were interested in constructing simple thiol-tethered benzoquinones 3 and chose as a convenient starting material 2,3-bis(bromomethyl)-1,4-dimethoxybenzene 2 (Scheme 1). Although this compound was first obtained as early as 1959 as a minor byproduct in the monobromination of 1, 2 and some nine years later in good yield by dibromination of 1, 3 these and all subsequent preparations of 2 have been conducted using N-bromosuccinimide (NBS) in carbon tetrachloride as solvent.…”