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. 2022 Jul 4;14(13):2738.
doi: 10.3390/polym14132738.

N-(2-Arylethyl)-2-methylprop-2-enamides as Versatile Reagents for Synthesis of Molecularly Imprinted Polymers

Monika Sobiech  1 , Dorota Maciejewska  1 , Piotr Luliński  1
Affiliations

N-(2-Arylethyl)-2-methylprop-2-enamides as Versatile Reagents for Synthesis of Molecularly Imprinted Polymers

Monika Sobiech et al. Polymers (Basel). .

Abstract

The paper describes the formation of six aromatic N-(2-arylethyl)-2-methylprop-2-enamides with various substituents in benzene ring, viz., 4-F, 4-Cl, 2,4-Cl2, 4-Br, 4-OMe, and 3,4-(OMe)2 from 2-arylethylamines and methacryloyl chloride in ethylene dichloride with high yields (46-94%). The structure of the compounds was confirmed by 1H NMR, 13C NMR, IR, and HR-MS. Those compounds were obtained to serve as functionalized templates for the fabrication of molecularly imprinted polymers followed by the hydrolysis of an amide linkage. In an exemplary experiment, the imprinted polymer was produced from N-(2-(4-bromophenyl)ethyl)-2-methylprop-2-enamide and divinylbenzene, acting as cross-linker. The hydrolysis of 2-(4-bromophenyl)ethyl residue proceeded and the characterization of material including SEM, EDS, 13C CP MAS NMR, and BET on various steps of preparation was carried out. The adsorption studies proved that there was a high affinity towards the target biomolecules tyramine and L-norepinephrine, with imprinting factors equal to 2.47 and 2.50, respectively, when compared to non-imprinted polymer synthesized from methacrylic acid and divinylbenzene only.

Keywords: N-acylation; molecularly imprinted polymers; phenethylamines; semi-covalent imprinting; tyramine.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of N-(2-arylethyl)-2-methylprop-2-enamides.
Figure 1
Figure 1
Schematic idea of the synthesis, employing a covalent strategy for the imprinting process and an adsorption process on the resultant imprinted polymer that is based on non-covalent interactions of the target analytes.
Figure 2
Figure 2
Lineweaver–Burk (a) and Freundlich (b) models for tyramine adsorption on MIPft and NIP.
Figure 3
Figure 3
SEM micrographs of MIPft (a,c,e,g) and NIP (b,d,f,h).
Figure 3
Figure 3
SEM micrographs of MIPft (a,c,e,g) and NIP (b,d,f,h).
Figure 4
Figure 4
EDS spectrum of MIPft before hydrolysis of the amide linkage (a), 13C CP MAS NMR spectrum for MIPft (b), nitrogen-sorption hysteresis (c) and pore-size distributions (d) for MIPft after hydrolysis of amide linkage.
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