Synthesis of aromatic 1,2-disulfonimides and their prospects as monomers?

New Journal of Chemistry Pub Date: 2023-02-10 DOI: 10.1039/D2NJ06005A

Abstract

The correlation between chemical structure and selective transport properties in polyimides led to the suggestion of poly-1,2-disulfonimides as prospective materials for high-performance diffusion membranes. Higher polarity along with steric features of the 1,2-disulfonimide fragment in comparison with the imide suggests a superior rate of inter-chain interactions along with presumably higher inter-planar distances in poly-1,2-disulfonimides. A structure of a novel 1,2-disulfonimide-containing dicarboxylchloride is proposed for the obtainment of high-molecular-weight polymers analogous to the routes utilised for the synthesis of poly(amide-imide)s. This article aims at the investigation of approaches for the synthesis of target 1,2-disulfonimide-fragment-containing monomers and the estimation of their properties using analytical and computational techniques. This article discloses the peculiarities of 1,2 disulfobenzoic acid chlorination, which leads to the substitution in the aromatic ring instead of the expected disulfonyl-chloride and instability of 1,2-disulfonimides during oxidation with potassium permanganate in various media.

Graphical abstract: Synthesis of aromatic 1,2-disulfonimides and their prospects as monomers
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