This study concentrates on the spectral and complexing properties of a tetraoxycalix[2]arene[2]triazine derivative bearing two bipyridines (Calix-BIPY2) in a mixture of acetonitrile∶chloroform (4∶1, V∶V). The results show that Calix-BIPY2 has a highly selectivity and sensitivity towards Zn 2＋ over various competing cations (K ＋ , Cu 2＋ , Cd 2＋ , Co 2＋ , Fe 2＋ , Hg 2＋ , Ag ＋ , Al 3＋ and Pb 2＋ ). The complexation of Zn 2＋ induces a remarkable fluorescence enhancement due to combination effects of the binding strength, electron spins state of metal ions, photoinduced charge transfer (PCT) and the rigidity of the complexing unit offered by calixarene-based hosts.

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In the macrocyclic title compound, C26H12Cl2N6O4, an O-atom-bridged calix[2]naphthalene­[2]triazine synthesized using a one-pot approach from naphthalene-2,7-diol and cyanuric chloride, the two isolated naphthalene planes and the two triazine-2,6-di­oxy planes adopt a 1,3-alternate configuration, with a dihedral angle of 84.10 (8)° between the naphthalene rings and a dihedral angle of 39.02 (14)° between the triazine rings. In the crystal, weak inter­molecular π–π stacking inter­actions are found between face-to-face naphthalene rings [centroid–centroid distance = 3.662 (7) Å].