Persulfurated Aromatic Compounds

Abstract

Persulfurated arenes have been known for about 50 years but they were underexploited in chemistry in spite of facile, mild, and high-yielding syntheses. Their properties (redox potentials, UV/Vis absorption, conductivity, nonlinear optical properties, etc.) are mainly due to the aromaticity of the ring with sp2-hybridized carbon atoms and to the electronic contribution from numerous divalent sulfur ligands, which also stabilize negative or positive charges. The characteristic conformational patterns of the sulfur ligands often facilitate preorganization in supramolecular assemblies, with or without thiophilic metal cations, for designing redox sensors, ion-selective membranes, clathrates, organic conductors, nonlinear optical materials, liquid crystals, coordination polymers, and bioinorganic systems. A new class of supramolecules with various molecular shapes such as asterisks, chains, wheels, and windmills were reported.

Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper‐Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers

“…[2d, 6, 7] Among these heterocyclic scaffolds, benzo [b]thiophenes [8] are of particular interest, as they are often found in biologically active molecules such as raloxifene [9] and potential drug candidates [10] and are also widespread in material chemistry. [11] Recently, Larock and co-workers applied a Pdcatalyzed iodocyclization for the elaboration of oligomeric benzo [b]thiophenes.…”

Functionalization of Quinoxalines by Using TMP Bases: Preparation of Tetracyclic Heterocycles with High Photoluminescene Quantum Yields

“…[18] Thus, severala nellation reactions were performed to substitute the electrophilic chlorine atoms with oxygen and sulfur.…”

New binucleating ligand with two [P,S] chelation pockets on a single phenyl ring: Syntheses and X-ray structures of 1,4-bis(diphenylphosphino)-2,5-difluoro-3,6-bis(methylthio)benzene and of bimetallic complex (CO)3Fe(μ-[(PPh2)(SMe)C6F2(SMe)(PPh2)])Fe(CO)3

“…The existence of 2 in two orientations is most likely due to the packing effects present in the solid state, as no signal separation corresponding to the presence of 2-a/2-b in solution was observed by low temperature NMR measurements ( 1 H and 31 P, À45°C, CDCl 3 ). Persulfurated aromatic derivatives have been shown to display varying substitution patterns resulting from different steric orientations of the -SR substituents around the central aromatic core [35], and this has been referred to as a solid state phenomenon, resulting from packing effects.…”