135883-45-3

Upstream product

• 135883-41-9 1-(tert-butylsulfanyl)-4-(trimethylsilylethynyl)benzene 
• 795274-48-5 1-tert-butylsulfanyl-4-(2'-triisopropylsilylethynyl)-benzene 
• 25752-90-3 tert-butyl 4-bromophenyl sulfide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 65688-19-9 1-(tert-butylsulfanyl)-4-iodobenzene 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 1402451-60-8 1,3-bis[(4-tert-butylthiophenyl)ethynyl]azulene 
• 1364344-62-6 2,6-bis[(4-acetylthiophenyl)ethynyl]naphthalene 
• 1364344-60-4 1,4-bis[(4-acetylthiophenyl)ethynyl]naphthalene 

Relevant academic research and scientific papers

Monitoring Solid-Phase Reactions in Self-Assembled Monolayers by Surface-Enhanced Raman Spectroscopy

Nanopatterned surfaces enhance incident electromagnetic radiation and thereby enable the detection and characterization of self-assembled monolayers (SAMs), for instance in surface-enhanced Raman spectroscopy (SERS). Herein, Au nanohole arrays, developed

Two-Terminal Molecular Memory through Reversible Switching of Quantum Interference Features in Tunneling Junctions

Large-area molecular tunneling junctions comprising self-assembled monolayers of redox-active molecules are described that exhibit two-terminal bias switching. The as-prepared monolayers undergo partial charge transfer to the underlying metal substrate (Au, Pt, or Ag), which converts their cores from a quinoid to a hydroquinoid form. The resulting rearomatization converts the bond topology from a cross-conjugated to a linearly conjugated π system. The cross-conjugated form correlates to the appearance of an interference feature in the transmission spectrum that vanishes for the linearly conjugated form. Owing to the presence of electron-withdrawing nitrile groups, the reduction potential and the interference feature lie close to the work function and Fermi level of the metallic substrate. We exploited the relationship between conjugation patterns and quantum interference to create nonvolatile memory in proto-devices using eutectic Ga–In as the top contact.

Bismuth(III)-Promoted Acetylation of Thioethers into Thioacetates

The thioacetate group is extensively employed as an anchoring group for attachment of molecules onto gold surfaces or between electrodes in molecular electronics. On account of its ready hydrolysis, it is often incorporated in the last step of a synthetic

Correlations between molecular structure and single-junction conductance: A case study with oligo(phenylene-ethynylene)-type wires

The charge transport characteristics of 11 tailor-made dithiol-terminated oligo(phenylene-ethynylene) (OPE)-type molecules attached to two gold electrodes were studied at a solid/liquid interface in a combined approach using an STM break junction (STM-BJ) and a mechanically controlled break junction (MCBJ) setup. We designed and characterized 11 structurally distinct dithiol-terminated OPE-type molecules with varied length and HOMO/LUMO energy. Increase of the molecular length and/or of the HOMO-LUMO gap leads to a decrease of the single-junction conductance of the linearly conjugate acenes. The experimental data and simulations suggest a nonresonant tunneling mechanism involving hole transport through the molecular HOMO, with a decay constant β = 3.4 ± 0.1 nm-1 and a contact resistance Rc = 40 k per Au-S bond. The introduction of a cross-conjugated anthraquinone or a dihydroanthracene central unit results in lower conductance values, which are attributed to a destructive quantum interference phenomenon for the former and a broken π-conjugation for the latter. The statistical analysis of conductance-distance and current-voltage traces revealed details of evolution and breaking of molecular junctions. In particular, we explored the effect of stretching rate and junction stability. We compare our experimental results with DFT calculations using the ab initio code SMEAGOL and discuss how the structure of the molecular wires affects the conductance values.

Formation of high-quality self-assembled monolayers of conjugated dithiols on gold: Base matters

This Article reports a systematic study on the formation of self-assembled monolayers (SAMs) of conjugated molecules for molecular electronic (ME) devices. We monitored the deprotection reaction of acetyl protected dithiols of oligophenylene ethynylenes (

Synthesis and properties of an anthraquinone-based redox switch for molecular electronics

The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cros

Synthetic protocols and building blocks for molecular electronics

Simple and readily accessible aryl bromides are useful building blocks for thiol end-capped molecular wires. Thus, 4-bromophenyl tert-butyl sulfide and 1-bromo-4-(methoxymethyl)benzene serve as precursors for a variety of oligo(phenylenevinylene) and olig

Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processes accessible, acetyl-protected thiols

The facile and efficient conversion of a tert-butyl protecting group to an acetyl protecting group for thiols by catalytic amounts of bromine in acetyl chloride and the presence of acetic acid has been developed. The fairly mild reaction conditions are of

Electric Current through a Molecular Rod - Relevance of the Position of the Anchor Groups

The electronic resistance of an electrode-molecule-electrode device strongly depends on the relative position of the anchor group in the molecular structure. The molecular rod, immobilized through two sulfur groups in the meta position on a pair of electr