Preparation and properties of novel aromatic poly(thioethers) derived from 4,4′-thiobisbenzenethiol

Abstract

SUMMARY: A series of amorphous and semicrystalline aromatic poly(thioethers) have been prepared by the reactions of 4,49-thiobisbenzenethiol and activated dihalides. Azo group activated dihalide monomer was prepared by the reactions of 4-fluoronitrosobenzene with a suitable diamine. The keto and phosphine sulfide containing monomers were synthesized by Friedel-Crafts acylation reactions of suitable halobenzenes with appropriate acid chlorides. Potassium carbonate mediated reactions in dimethylacetamide afforded moderate to high molecular weight polymers. Polymers with high melting points were prepared by using diphenyl sulfone as a co-solvent. The poly(thioethers) exhibit high glass transition temperatures and/or high melting points. In addition, the polymers exhibit excellent thermal stability.

Development of High Refractive Index Plastics

“…Based on molar refraction and molar dispersion, sulfur [53][54][55] and oxygen containing polymers would be expected to have higher refractive index and Abbe number values [48,49].…”

“…Refractive index can also be achieved through polarizabilities of the combined groups in a molecule [53][54][55].…”

“…The novel way to increase the refractive index of optical polymers is reported to be by the introduction of atoms having high atomic weight such as sulfur in the polymer structure [53][54][55]. Sulfur containing monomers are good candidates for producing high refractive index optical materials; ready polarizability of a sulfur produces a strong interaction between the material and incident light, resulting in high refractive index [55].…”

Synthesis and characterization of sulfonated poly(arylene thioether)s and their blends with polybenzimidazole for proton exchange membranes

“…However, the chemical stabilities of the poly(arylene ether)s membranes against hydrogen peroxide treatment were not satisfactory, which encouraged us to investigate thioether polymeric materials. A series of poly(thioether)s were prepared by McGrath and coworkers [20] who showed that the aromatic (thioether)s possessed high glass transition temperatures and melting points as well as excellent thermal stability. For PEM based fuel cell applications, sulfonated poly(arylene thioethersulfone)s with different sulfonation degrees were synthesized and characterized in terms of proton conductivity, methanol permeability, mechanical and thermal stability [21,22].…”

Proton conductivity and properties of sulfonated polyarylenethioether sulfones as proton exchange membranes in fuel cells

“…Much effort has been expended in the development of new proton conducting polymers by direct polymerization. The sulfonic acid groups were attached onto highly stable aromatic polymers, such as poly(ether ether ketone) [8], polyethersulfone [9,10], polyimide [11], and poly(phenylene sulfide) [12]. These polymers generally exhibit good thermal and chemical stabilities and high proton conductivities.…”