Thiabicyclononane-Based Antimicrobial Polycations Zhishuai Geng M. G. Finn 10.1021/jacs.7b07596.s001 https://acs.figshare.com/articles/journal_contribution/Thiabicyclononane-Based_Antimicrobial_Polycations/5518837 Bicyclo­[3.3.1]­nonane (BCN) polycations were synthesized by the reaction of the bivalent electrophile thiabicyclo[3.3.1]­nonane dinitrate with a series of simple bis­(pyridine) nucleophiles. Oligomers of moderate chain length were formed in a modular approach that tolerated the inclusion of functionalized and variable-length linkers between the pyridine units. Post-polymerization modification via copper-catalyzed azide–alkyne cyloaddition was enabled by the inclusion of terminal alkyne groups in these monomers. Most of the resulting polymers, new members of the polyionene class, inhibited the growth of bacteria at the μg/mL level and killed static bacterial cells at polymer concentrations of tens of ng/mL, with moderate to good selectivity with respect to lysis of red blood cells. While resistance to the BCN polymers was developed only very slowly over multiple passages, a degradable version of the polycation was observed to make <i>E. coli</i> cells more susceptible to other quaternary ammonium based antimicrobials. Solid substrates (glass and crystalline silicon) covalently functionalized with a representative BCN polycation were also able to repetitively kill bacteria in solution at high rates and with cleaning by simple sonication between exposures. 2017-10-19 20:45:05 chain length covalently functionalized variable-length linkers representative BCN polycation coli cells terminal alkyne groups bacteria inclusion blood cells BCN polymers polyionene class Post-polymerization modification polymer concentrations degradable version pyridine units Solid substrates quaternary ammonium