Clickable Molecularly Imprinted Carboxylated Phenolic‐Furan Polymer for Selective Recognition of (+)‐Sertraline

ABSTRACT This work reports the synthesis of a molecularly imprinted phenolic formaldehyde resin for enantioselective recognition of the cationic (+)‐sertraline (ST) enantiomer. The polymeric material was synthesized via polymerizing p‐hydroxybenzoic acid (4‐HBA) and 4‐(((furan‐2‐ylmethyl)amino)methyl)phenol (Ph‐NH‐Fu) with formaldehyde in acidic medium and further post‐crosslinking via Diels–Alder (DA) cycloaddition with bis(maleimido)ethane (BMO) for improved stability and selective binding. The optimized adsorption conditions (pH 6–8) resulted in a maximum adsorption capacity of 433 mg/g, with adsorption behavior following the Langmuir model. Selectivity studies revealed that the imprinted polymer (+)‐ST‐IP exhibited a 14‐fold higher affinity for (+)‐ST than the nonimprinted polymer (NIP), confirming the success of molecular imprinting. Column separation techniques indicated (+)‐ST‐IP to be 97% enantiomeric excess (ee) of eluted (−)‐ST, whereas NIP was non‐enantioselective. Structural characterization revealed the creation of the specific recognition sites, and thermal analysis demonstrated the stability of the crosslinked polymer. The findings indicate the promise of (+)‐ST‐IP as a highly effective sorbent for application in pharmaceuticals, especially chiral purification of drugs from racemic mixtures.