Designing of molecularly imprinted polymer with carboxylic acid functionality for chiral separation of (±)‐3,4‐methylenedioxymethamphetamine

Abstract

In this work, we discuss the development of a long‐lasting enantioselective material for the effective enantio‐recognition of S‐3,4‐methylenedioxymethamphetamine (S‐MDMA) and chiral separation of the (±)‐MDMA racemate using a cross‐linked poly(acrylic acid‐4‐vinylpyridine) copolymer. The first step was the synthesis and characterization of an acryloyl‐S‐MDMA (Ac‐S‐MDMA) amide. After that, the free radical initiator AIBN was used to copolymerize the synthesized chiral amide with 4‐vinylpyridine and divinylbenzene. The incorporated S‐MDMA species were extracted from the polymeric particles by heating them with sodium hydroxide, followed by rinsing with hydrochloric acid. This developed the molecularly imprinted S‐MDMA‐IP particles, which were visualized with a scanning electron microscope (SEM) and FTIR spectra. The selectivity parameters indicated a higher affinity of the fabricated S‐MDMA‐IP toward S‐MDMA, around ten‐fold higher than that related to R‐MDMA. Results from Langmuir adsorption experiments at pH 6 demonstrated a maximal capacity of 142 mg/g. In addition, the values of enantiomeric excess were found to be 94.5% and 79.4% for R‐ and S‐MDMA in the loading and eluant solutions, respectively, after optical separation was done using the column technique.

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