Comparative DFT-D3 assessment of fluorogenic supramolecular interaction of naphthalene moiety location on new dibenzodiaza-crown ether macrocycles with C60

•A new family of dibenzodiaza-crowns ligands appended with naphthalene moiety is designed and synthesized.•The calculated and experimental KFL values for the Ln/C60 dyads are compared with their parent macrocycles and their dinaphthodiaza-crowns homologs.•-The results revealed that the naphthalene groups are more efficient as a part of the macrocycle than the side arm.•Their supramolecular interactions of Ln/C60 dyads are evaluated by DFT-B97D3 calculation.•The comparison of the experimental measurements with these calculations indicated good agreements of thermodynamic results in the gas phase and solution.