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A series of comb-like ionenes (C-ionenes) with aliphatic side chains were prepared via the Menschutkin reaction from amine, epichlorohydrin, and N, N, N′, N′-tetramethyl-1,6-hexanediamine. The structures of the resulting ionenes were characterized by means of charge density, H-NMR, and C-NMR. The antimicrobial properties of the ionenes were also investigated by measuring the minimum inhibition concentration (MIC) against Escherichia coli ( E. coli). The corresponding antimicrobial dynamics were studied by detecting the UV absorbance of the E. coli suspension. It was found that in comparison to the linear ionenes (L-ionenes), C-ionenes exhibited lower MIC values and faster antimicrobial effect influenced by the side chains. In particular, C-ionene with 4-carbon side chains showed MIC at 7.8 μg/mL and its aqueous solution (31.2 μg/mL) inhibited 99.9 % E. coli within 2 min. The morphologies of C-ionenes in aqueous solution were investigated by measuring their particle sizes and zeta potentials. In addition, the anti-mold tests against Aspergillus niger and Chaetomium globosum suggested that the comb-like ionenes were effective at inhibiting the growth of the fungi. [ABSTRACT FROM AUTHOR]