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Artificial transmembrane anion transporters have emerged as promising supramolecular scaffolds in this context, having demonstrated membrane activity in mammalian systems and showing growing potential in antimicrobial research. Here, we report a series of heterocycle\u2010fused squaramide anionophores capable of binding and transporting chloride. Several members of this series display measurable antimicrobial activity, alongside evidence of intracellular chloride modulation in bacterial cells. 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