Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

Abstract

The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylenevinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

Oxidative Electrochemical Switching in Dithienylcyclopentenes, Part 2: Effect of Substitution and Asymmetry on the Efficiency and Direction of Molecular Switching and Redox Stability

“…To circumvent this, 4 H was prepared [19] by Suzuki coupling of A with 1-bromo-4-tert-butylthiobenzene (B) to yield C (45 %). Subsequent substitution of the tBu groups by acetyl groups provided 4 H. [20] The dialdehyde 9 F was obtained by lithiation [18] of 8 F, followed by quenching with DMF. Compound 12 H was obtained by esterification of the corresponding diacid in ethanol with a catalytic amount of 30 % aqueous HCl.…”

Single-molecule transport in three-terminal devices

“…OPV-5 consists of five benzene rings that are connected through double bonds [71]. The molecule has alkane side arms to make it soluble in common solvents.…”

Efficient and Rapid Solvent‐Free Acetylation of Alcohols, Phenols, and Thiols Using Catalytic Amounts of Sodium Acetate Trihydrate

“…We next decided to use this chemistry for the protection of thiols due to the importance of their masking 4 Journal of Chemistry [49], and electrochemistry [50,51]. Therefore, thiophenol, 4-chlorothiophenol, naphthalene-2-thiol, phenylmethanethiol, and furan-2-ylmethanethiol were conveniently acetylated in less than 1 h under the conditions similar to those employed for alcohols ( Table 2).…”