Two structurally simple Pt(II)‐directed self‐assembly loop complexes were prepared by reactions of cis‐(PEt3)2Pt(OTf)2 and the corresponding pyridylamide‐functionalized pyridyl ligands. Both Pt(II)‐based complexes exhibit singlet fluorescence, indicating that the platinum metal serves only as a structural, rather than a direct photophysical role within the loop framework. The crystal structure of complex 1 shows a distorted loop conformation with a hydrophobic pocket defined by the bridging ligands. The anion binding affinities of these two complexes were investigated with a range of anions. Such studies using UV–vis absorption, fluorescence, and 1H NMR titrations showed that complex 1 exhibits excellent binding sensitivity and selectivity for benzoate over acetate in solution via a combination of electrostatic, hydrogen‐bonding, and π–π interactions, whereas complex 2 shows comparable binding affinities toward acetate and benzoate due to the lack of favorable aromatic π–π interaction.