| Summary: | We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C<sub>60</sub>(>ME<sub>1</sub>N<sub>6</sub><sup>+</sup>C<sub>3</sub>) (<strong>1</strong>) and C<sub>60</sub>(>ME<sub>3</sub>N<sub>6</sub><sup>+</sup>C<sub>3</sub>) (<strong>2</strong>), with variation of the methoxyethyleneglycol length. Each of these derivatives bears a well-defined number of cationic charges aimed to enhance and control their ability to target pathogenic Gram-positive and Gram-negative bacterial cells for allowing photodynamic inactivation. The synthesis was achieved by the use of a common synthon of pentacationic <em>N,N′,N,N,N,N</em>-hexapropyl-hexa(aminoethyl)amine arm (C<sub>3</sub>N<sub>6</sub><sup>+</sup>) having six attached propyl groups, instead of methyl or ethyl groups, to provide a well-balanced hydrophobicity–hydrophilicity character to pentacationic precursor intermediates and better compatibility with the highly hydrophobic C<sub>60</sub> cage moiety. We demonstrated two plausible synthetic routes for the preparation of <strong>1</strong> and <strong>2</strong> with the product characterization via various spectroscopic methods.
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