One-pot synthesis of highly selective phenylboronic acid-functionalized organic polymers for the enrichment of cis -diol containing molecules

Boronate affinity materials (BAMs) are gaining increasing attentions in the fields of separation, sensing, imaging, diagnostic, and drug delivery. However, poor selectivity caused by non-specific adsorption is still a shortcoming of the present BAMs, particularly organic BAMs. In this work, by investigating the effects of polymerization solvents and crosslinker types on binding selectivity of the PBA-functionalized polymers, we found that the phenylboronic acid (PBA)-functionalized polymers using N,N’ -methylbisacrylamide (MBAA) as the crosslinker synthesized in DMSO by one-pot polymerization approach displayed ultrahigh selectivity to the cis -diol containing molecules. The physical features of all the polymers were characterized in detail. The PBA-MBAA particles synthesized in DMSO showed a high binding affinity with dissociation constants of 2.0 × 10 –4 M and 9.8 × 10 –5 M to adenosine and catechol, respectively, and a relatively high binding capacity (46 ± 1 μmol/g for adenosine and 166 ± 12 μmol/g for catechol). Binding kinetics measurement demonstrated that such PBA-MBAA particles required a long time (30 min) to reach the adsorption equilibrium due to their microporous structure. The recovery rates for the extraction of nucleosides by this polymer were high (63 ~ 88%, n = 3). In general, selection of MBAA as the crosslinker and DMSO as the polymerization solvent is opt to obtain highly selective BAMs, such protocol can be employed not only for producing BAMs for separation, but also making fluorescent BAM nanoparticles for sensing and imaging. Graphical abstract