Porous Polymers Containing Metallocalix[4]arene for the Extraction of Tobacco-Specific Nitrosamines

Abstract

We designed porous polymers with a tungsten-calix[4]arene imido complex as the nitrosamine receptor for the efficient extraction of tobacco-specific nitrosamines (TSNAs) from water. The interaction between the metallocalix[4]arene and the TSNA, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (nicotine-derived nitrosamine ketone, NNK) was investigated. We found that the incorporation of the nitrosamine receptor into porous polymers increased their selectivity toward NNK over nicotine. The polymer with an optimal ratio of calixarene-containing and porosity-inducing building blocks showed a high maximum adsorption capacity of up to 203 mg/g toward NNK under sonication, which was among the highest values reported. The adsorbed NNK could be removed from the polymer by soaking it in acetonitrile, enabling the adsorbent to be reused. A similar extraction efficiency to that under sonication could be achieved using the polymer-coated magnetic particles under stirring. We also proved that the material could efficiently extract TSNAs from real tobacco extract. This work not only provides an efficient material for the extraction of TSNAs but also offers a design strategy for efficient adsorbents.

Bioinspired Organic Porous Coupling Agent for Enhancement of Nanoparticle Dispersion and Interfacial Strength

“…Its unique concave polymer backbone hinders dense packing, resulting in high surface areas and good solubility in various organic solvents. Known as polymers of intrinsic microporosity (PIMs), these processable porous polymers are widely used in gas separation and extraction of tobacco-specific nitrosamines. − A notable feature of this polymer is its ability to be easily functionalized using norbornyl and anthracenyl end groups. The initial step involves a Diels–Alder reaction between the anthracenyl group and N -phenyl-maleimide.…”