Discovery and Development of One Monomer Molecularly Imprinted Polymers (OMNiMIPs)

Molecularly imprinted polymers (MIPs) are polymeric receptors for a targeted template molecule that are traditionally formed using a combination of functional monomers and crosslinkers. While investigating novel crosslinkers for MIPs, one of these (2-(methacryloylamino)ethyl-2-methylacrylate (referred to as N,O-bismethacryloyl ethanolamine or "NOBE")) performed better when used alone versus in combination with other monomers. This introduced the concept of one monomer molecularly imprinted polymers, given the acronym OMNiMIPs, and prompted studies provided in this report that clarify OMNiMIPs have fundamental differences compared to traditionally formulated MIPs. Enantioselectivity studies using BOC-L-tyrosine as a standard template showed that NOBE OMNiMIPs afforded higher-performing MIPs compared with traditional MIPs, have significantly higher binding capacities, and have an internal hydrogen-bonded crosslinking structure that contributes to the morphological stability of the binding site structure. Based on the adventitious discovery of NOBE OMNiMIPs, new analogs based on the NOBE structure were developed and evaluated for further enhancement of molecular recognition performance and novel capabilities of OMNiMIPs. While the majority of the new OMNiMIPs exhibited enantiomeric selectivity toward BOC-L-tyr, improvements were not observed compared with NOBE.