Supporting Information

Synthesis, characterization and antibacterial activity of heterocyclic quaternary ammonium polymers

Hodaya Shadmona, Arijit Basua, Lea H. Eckhardb, Abraham J. Domba*, Nurit Beythb*

aInstitute for Drug Research, School of Pharmacy-Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, IsraelbDepartment of Prosthodontics, School of Dentistry, Faculty of Dental Medicine, The Hebrew University of Jerusalem, Jerusalem, Israel

Proton NMR and FTIR spectra for the synthesized compoundsDSC thermograms for the polymers

Electronic Supplementary Material (ESI) for New Journal of Chemistry.This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

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1H-NMR

Figure 1. 1H-NMR spectrum of linear PVI

Figure 2. 1H-NMR spectrum of C1-alkylated PVI

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Figure 3. 1H-NMR spectrum of C4-alkylated PVI

Figure 4. 1H-NMR spectrum of C6-alkylated PVI

Figure 5. 1H-NMR spectrum of C8-alkylated PVI

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Figure 6. 1H-NMR spectrum of C10-alkylated PV

Figure 7. 1H-NMR spectrum of C18-alkylated PVI

Figure 8. 1H-NMR spectrum of linear PVT

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Figure 9. 1H-NMR spectrum of C8-alkylated PVT

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FTIR

Figure 10. FTIR spectra for A) linear PVI B) C1-alkylated PVI C) C4-alkylated PVI D) C6-alkylated PVI E) C8-alkylated PVI F) C10-alkylated PVI G) C18-alkylated PVI.

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Figure 11. FTIR spectra for A) cross linked PVI B) C1-alkylated cross linked PVI C) C4-alkylated cross linked PVI D) C6-alkylated cross linked PVI E) C8-alkylated cross linked PVI F) C10-alkylated cross linked PVI G) C18-alkylated cross linked PVI.

Figure 12. FTIR spectra for A) linear PVT B) C8-alkylated PVT C) cross linked PVT D) C8-alkylated cross linked PVT.

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Figure 13. DSC thermograms comparison of different alkylated Polyvinyl Imidazoles

Figure14. Comparison between crosslinked Polyvinyl imidazole and Poly ethylene imine.

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Figure 15. Comparison between linear Polyvinyl imidazole and branched Poly ethylene imine.

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Table 1. Antibacterial effect on S. mutans and L. casei evaluated using the agar diffusion test (ADT).

Tested material S. mutans L. caseiLinear PVI 0 0C1-alkylated PVI 0 0C4-alkylated PVI 0 0C6-alkylated PVI 0 0C8-alkylated PVI 0 0C10-alkylated PVI 0 0C18-alkylated PVI 0 0Crosslinked PVI 0 0C1-alkylated crosslinked PVI 0 0C4-alkylated crosslinked PVI 0 0C6-alkylated crosslinked PVI 0 0C8-alkylated crosslinked PVI 0 0C12-alkylated crosslinked PVI 0 0C18-alkylated crosslinked PVI 0 0Linear PVT 0 0C8-alkylated PVT 0 0Crosslinked PVT 0 0C8-alkylated crosslinked PVT 0 0Composite resin 0 0Control (Doxycycline) 0.3±0.5 0.3±0.3

Inhibition zone diameter (mm) was measured in two perpendicular lines and the diameter of the tested sample was subtracted.