Jump to main content
Jump to site search

Issue 5, 2014
Previous Article Next Article

Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer–template interactions in imprinting of 1,2,3-trichlorobenzene

Author affiliations

Abstract

The interactions between each component of the pre-polymerisation mixtures used in the synthesis of molecularly imprinted polymers (MIP) specific for 1,2,3,4,5-pentachlorobenzene (1) and 1,2,3-trichlorobenzene (2) were examined in four molecular dynamics simulations. These simulations revealed that the relative frequency of functional monomer–template (FM–T) interactions was consistent with results obtained by the synthesis and evaluation of the actual MIPs. The higher frequency of 1 interaction with trimethylstyrene (TMS; 54.7%) than 1 interaction with pentafluorostyrene (PFS; 44.7%) correlated with a higher imprinting factor (IF) of 2.1 vs. 1.7 for each functional monomer respectively. The higher frequency of PFS interactions with 2 (29.6%) than TMS interactions with 2 (1.9%) also correlated well with the observed differences in IF (3.7) of 2 MIPs imprinted using PFS as the FM than the IF (2.8) of 2 MIPs imprinted using TMS as the FM. The TMS–1 interaction dominated the molecular simulation due to high interaction energies, but the weaker TMS–2 resulted in low interaction maintenance, and thus lower IF values. Examination of the other pre-polymerisation mixture components revealed that the low levels of TMS–2 interaction was, in part, due to interference caused by the cross linker (CL) ethyleneglycol dimethylacrylate (EGDMA) interactions with TMS. The main reason was, however, attributed to MeOH interactions with TMS in both a hydrogen bond and perpendicular configuration. This positioned a MeOH directly above the π-orbital of all TMS for an average of 63.8% of MD2 creating significant interference to π–π stacking interactions between 2 and TMS. These findings are consistent with the deviation from the ‘normal’ molecularly imprinted polymer synthesis ratio of 1 : 4 : 20 (T : FM : CL) of 20 : 1 : 29 and 15 : 6 : 29 observed with 2 and TMS and PFS respectively. Our molecular dynamics simulations correctly predicted the high level of interference from other MIP synthesis components. The effect on PFS–1 interaction by MeOH was significantly lower and thus this system was not adversely affected.

Graphical abstract: Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer–template interactions in imprinting of 1,2,3-trichlorobenzene

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Dec 2013, accepted on 05 Dec 2013 and first published on 05 Dec 2013


Article type: Paper
DOI: 10.1039/C3OB42399A
Author version
available:
Download author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 844-853
  •   Request permissions

    Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer–template interactions in imprinting of 1,2,3-trichlorobenzene

    D. Cleland, G. D. Olsson, B. C. G. Karlsson, I. A. Nicholls and A. McCluskey, Org. Biomol. Chem., 2014, 12, 844
    DOI: 10.1039/C3OB42399A

Search articles by author

Spotlight

Advertisements