Synthesis and properties of polysulfonamides containing thiophene links

Abstract

SynopsisIn order to study the synthesis and properties of polysulfonamides containing thiophene links, 2,2-bis(5-chlorosulfonyl-2-thienyl)propane [BCTP], 2,2-bis(5-chlorosulfonyl-2-thienyl)butane [BCTB], 1,1-bis(5-chlorasulfonyl-2-thienyl)cyclohexane [BCTC], and 2,4-dichlorosulfonyl thiophene [DCST] were prepared and interfacial polycondensations with various aliphatic diamines were carried out. The resulting polymers had inherent viscosities in the range of 0.13-0.41 dL/g and showed high extent of moisture absorptions. Most of the polysulfonamides were soluble in electron-donating solvents such as pyridine, DMF, DMSO, NMP, etc. These polysulfonamides exhibited relatively good thermal stabilities. The TGA data revealed 5% weight losses at 275-405°C and residual weights at 500°C were 13-40% under nitrogen. It was also found that dithienyldisulfonyl chlorides produced more thermally stable polymers than E S T , which were comparable to common polysulfonamides from aromatic disulfonyl chlorides.

Organocatalytic Synthesis of Polysulfonamides with Well-Defined Linear and Brush Architectures from a Designed/Synthesized Bis(N-sulfonyl aziridine)

“…High-molar-mass polysulfonamides are usually achieved by the interfacial polycondensation technique, limiting large-scale preparation. 10,11 Other methods have also been developed, for example, the ring-opening polymerization (ROP) of ethanesultam with water catalysis, 12 polycondensation of active di-1-benzotriazolyl disulfonate with an aromatic diamine, 13 and ROP of N-(methanesulfonyl)azetidine. 14 Unfortunately, these monomers are prepared by tedious procedures.…”

“…Conventionally, polysulfonamides are synthesized by the reaction of disulfonyl chlorides with various diamines (Scheme a). − However, this method suffers from certain limitations, such as narrow monomer scope, the low molar mass of polysulfonamides, and a harmful byproduct (HCl) generation. High-molar-mass polysulfonamides are usually achieved by the interfacial polycondensation technique, limiting large-scale preparation. , Other methods have also been developed, for example, the ring-opening polymerization (ROP) of ethanesultam with water catalysis, polycondensation of active di-1-benzotriazolyl disulfonate with an aromatic diamine, and ROP of N -(methanesulfonyl)­azetidine . Unfortunately, these monomers are prepared by tedious procedures.…”