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

Three copolymers TCP1-3 bearing Trӧger's base (TB) units intercalated with various thioether groups were synthesized using a catalyst-free thiol-yne click reaction. TCP1-3 display excellent solubility in common organic solvents allowing for their structural, and photophysical characterization. The thioether groups in TCP1-3 were selectively oxidized into their respective sulfone derivatives under mild oxidation reaction conditions affording the postmodified copolymers TCP4-6. Investigation of organic dye uptake from water by TCP1-6 proved 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 copolymers TCP4-6 display superior and faster MEB removal efficiencies with respect to their corresponding synthons TCP1-3.