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The new symmetric acyclic <i>N,N’</i>-bis(1-pyrenyl) squaramide (<b>H₂L</b>) functionalized with the pyrene moiety as a fluorogenic fragment has been designed and its ability to selectively detect specific anions and metals investigated. <b>H₂L</b> selectively binds Cl⁻ both in solution (DMSO 0.5% H₂O and MeCN) and in the solid state, and allows to selectively detect Cu²⁺ in MeCN with the formation of a 2:1 metal-receptor complex, with a green intense emission appreciable by naked eye under the UV lamp. The <b>H₂L</b> copper complex preserves its emission properties in the presence of Cl⁻. The addition of basic anions (OH⁻, CN⁻, and F⁻) up to 10 equivalents caused the deprotonation of the squaramide NHs and a dramatic change of the emission properties of the <b>H₂L</b> copper complex.