Selective removal of toxic organic dyes using Trӧger base-containing sulfone copolymers made from a metal-free thiol-yne click reaction followed by oxidation

Abstract

Three copolymersTCP1-3bearing Trӧger's base (TB) units intercalated with various thioether groups were synthesized using a catalyst-free thiol-yne click reaction.TCP1-3display excellent solubility in common organic solvents allowing for their structural, and photophysical characterization. The thioether groups inTCP1-3were selectively oxidized into their respective sulfone derivatives under mild oxidation reaction conditions affording the postmodified copolymersTCP4-6. Investigation of organic dye uptake from water byTCP1-6proved their efficiency as selective adsorbents removing up to 100% of the cationic dye methylene blue (MEB) when compared to anionic dyes, such as Congo red (CR), methyl orange (MO) and methyl blue (MB). The sulfone-containing copolymersTCP4-6display superior and fasterMEBremoval efficiencies with respect to their corresponding synthonsTCP1-3.