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This research includes the design and synthesis of new derivatives for rhodanine azo compounds (<b>4a</b><b>&#8722;</b><b>c</b>) containing a naphthalene ring. Physiochemical properties of the synthesized compounds were determined by their melting points, FTIR, ¹H-NMR, ¹³C-NMR, and elemental analysis spectroscopic techniques. The biological activities of the newly prepared azo rhodanine compounds were evaluated against some pathogenic bacteria using three different bacterial species including (<i>E</i><i>scherichia</i><i> coli</i>., <i>P</i><i>seudomonas</i><i> aeruginosa</i>, <i>S</i><i>taphylococcus</i><i> aureus</i>) and compared with amoxicillin as a reference drug. The results showed that our compounds have moderate-to-good vital activity against the mentioned pathogenic bacteria. The selectivity and sensitivity of the newly prepared rhodanine azo compounds with transition metals Co²⁺, Cu²⁺, Zn²⁺, Ni²⁺, and Fe³⁺ were studied using UV&#8722;vis and fluorescence spectroscopy techniques. Among the synthesized azos, azo <b>4</b><b>c</b> showed affinity toward Fe³⁺ ions with an association constant of 4.63 &#215; 10⁸ M^&#8722;1. Furthermore, this azo showed high sensitivity toward Fe³⁺ ions with detection limits of 5.14 &#181;M. The molar ratio and Benesi&#8722;Hildebrand methods confirmed the formation of complexes between azo<b> 4</b><b>c</b> and Fe³⁺ with 1:2 binding stoichiometry. Therefore, azo <b>4</b><b>c</b> showed excellent potential for developing efficient Fe³⁺ chemosensors.