221292-39-3

Upstream product

• 106-53-6 para-bromobenzenethiol 
• 754-05-2 ethenyltrimethylsilane 
• 16241-06-8 O-(4-bromophenyl) N,N-dimethylcarbamothioate 
• 7305-13-7 S-(4-bromophenyl) dimethylcarbamothioate 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 1220572-77-9 4-[2-(trimethylsilyl)ethylsulfanyl]phenylboronic acid 
• 221292-45-1 2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide 
• 221292-43-9 2-(trimethylsilyl)ethyl-4'-<(trimethylsilyl)ethynyl>phenyl sulfide 

Relevant academic research and scientific papers

Importance of the Anchor Group Position (Para versus Meta) in Tetraphenylmethane Tripods: Synthesis and Self-Assembly Features

The efficient synthesis of tripodal platforms based on tetraphenylmethane with three acetyl-protected thiol groups in either meta or para positions relative to the central sp3carbon for deposition on Au (111) surfaces is reported. These platfor

Enhanced Separation Concept (ESC): Removing the Functional Subunit from the Electrode by Molecular Design

A new concept to improve the reliability of functional single molecule junctions is presented using the E-field triggered switching of FeIIbis-terpyridine complexes in a mechanically controlled break junction experiment as model system. The complexes comprise a push-pull ligand sensing the applied E-field and the resulting distortion of the FeII ligand field is expected to trigger a spin-crossover event reflected in a sudden jump of the transport current. By molecular engineering, the active centre of the complex is separated from the gold electrodes in order to eliminate undesired side-effects. Two aspects are considered to isolate the central metal ion, namely the spacing by introducing additional alkynes, and the steric shielding achieved by bulky isopropyl groups. With this small series of model complexes, a pronounced correlation is observed between the occurrence of bistable junctions and the extent of separation of the central metal ion, affirming the hypothesized Enhanced Separation Concept (ESC).

4,4″-disubstituted terpyridines and their homoleptic FeII complexes

A novel synthetic route to 4,4″-disubstituted-2,2′:6′, 2″-terpyridine ligands by Suzuki-Miyaura cross-coupling was elaborated by synthesizing compounds 4a-5c. The considerable stability of 4-substituted lithium triisopropyl 2-pyridylborates 2a-c, which are less prone to protodeboronation than similarly functionalized neutral boronic acid derivatives, enabled this synthetic route. The terpyridine core structure was further functionalized by exposing 4,4″-dichloroterpyridine (4b) to Suzuki coupling conditions to yield 4,4″-diarylterpyridines 5a-c. Homoleptic FeII complexes 8a-f of the reported terpyridine ligands were formed quantitatively, which demonstrates the lack of steric repulsion of substituents at the 4- and 4″-positions during complexation. The solid-state structures of particular ligands and FeII complexes were analyzed by single-crystal X-ray crystallography. UV/Vis absorption data for the Fe II complexes are also provided to complement the results reported here. A novel synthetic route to terpyridine ligands is reported. Pyridine building blocks are interlinked by Suzuki-Miyaura cross-coupling reactions. The potential of the method is demonstrated by assembling the 4,4″- disubstituted terpyridine ligands shown, which are subsequently converted into their homoleptic FeII complexes. Copyright

Oligoaryl cruciform structures as model compounds for coordination-induced single-molecule switches

The synthesis of two new cruciform structures 3 and 4 comprising an oligo(phenylene-vinylene) (OPV) and a perpendicular oligoaryl bar - namely an oligophenylene (OP) (3) and a naphthyl-phenyl-naphthyl system (4) - is reported. The OPV rod consists of two terminal pyridine units, whereas the oligoaryl rod bears two terminal acetylsulfanyl groups as protected anchor groups. The OPV bar was assembled via a Homer-Wadsworth-Emmons reaction, which directly led to the desired E,E isomers. The perpendicular oligoaryl bars were assembled with a Suzuki reaction using the corresponding boronic acids, which were already fitted with an ethyl-trimethylsilane (ethyl-TMS) sulfanyl group. In a last step, the ethyl-TMS-protected sulfur atoms were transpro-tected to the thioacetyl units. The cruciform structures 3 and 4 are model compounds to investigate a coordinationinduced single-molecule switch exploiting the potentialdependant different bonding strengths of the anchor groups to gold. Metal-molecule-metal junctions were formed using a mechanically controllable break junction (MCBJ) setup. Current traces of molecular junctions were statistically analyzed. Further investigations of model compounds consisting only of the single bar confirm that individual molecules carrying the required function for the switching experiments were trapped between two electrodes and were mainly immobilized via thiol-gold anchor bonds.

Novel cruciform structures as model compounds for coordination induced single molecule switches

We have synthesized various molecular cruciforms consisting of two different crossing π-systems and comprising crosswise arranged thiol- and pyridine-anchor groups. With these model compounds we strive towards the investigation of a new switching concept based on the potential dependent coordination of pyridines to gold electrodes in an electrochemical set-up. Integration of these cruciform molecules between both electrodes of a mechanically controlled break junction in a liquid environment gave insight into their single molecule transport properties. These studies allowed individual transport characteristics to be assigned to the bar subunits of the cruciforms but also revealed the remaining experimental challenges to realize the suggested switching concept. Schweizerische Chemische Gesellschaft.

2-(trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions

The present report describes the novel and smooth generation of sulfenate salts by fluoride-mediated cleavage of 2-(trimethylsilyl)ethyl sulfoxides. Efficiency of the process was elucidated through further reaction with alkyl halides to give stable sulfox

Soluble ferrocene conjugates for incorporation into self-assembled monolayers

A series of phenylethynyl oligomers (I-V) possessing a ferrocene and thiol at each termini have been synthesized. These oligomers have been designed to overcome the inherent insolubility of this class of complexes by substitution at the phenyl groups with methyl and propoxy substituents. Several new reactions for preparing arenethiol-protected compounds are described. Interestingly, the generation of an arenethiol anion during base- or fluoride-catalyzed deprotection has been characterized.