Synthesis and characterization of novel Tröger’s base containing polymers from commercial available diamines

Abstract

For potential use as multifunctional nitrogen containing polymers in catalysts, antimicrobial and microporous materials, three novel step growth polymers containing Troger’s base (TBPs) were designed and synthesized by typical Troger’s Base condensation using cheap commercial available aromatic diamine sources including 4,4′-diaminodiphenylmethane (MDA), 4,4′-diaminodiphenyl ether (4,4’-ODA), and 4,4′-(hexafluoroisopropylidene)dianiline (BisAAF). FT-IR, 1H NMR, and GPC analysis were employed to obtain the compositional and structural information. Both TBP-1 and TBP-2 were insoluble in most common organic solvents whereas TBP-3, haloalkanes, held more promising solubility. The number average molecular weights (Mn) of all three TBPs were close to 30,000 g/mol. Thermal properties were gained from TGA and DSC measurements. TBP-1 and TBP-3 were relatively more thermal stable than TBP-2 while their overall T d (5%) were less than 200°C. The glass transition temperatures for all three TBPs were not observed between room temperature and their thermal decomposition. Protonation of TBP-1 was attempted and revealed the instability of quaternized Troger’s base structures.