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Carboxylic acid supramolecular synthon exhibited dimer or catemer motifs in the crystal lattice depend on the substituent and other functional groups present in the structure. In general, presence of other competing functional groups produced catemer motifs, whereas unsubstituted acids showed dimer. In this manuscript, we have synthesized a new aryl ether amine-based Schiff base with carboxylic acid functionality (1) and demonstrated polymorphic structure via catemer (1a) and dimer (1 b) motifs in the solid state. In both the structure, carboxylic acid group adopted different orientation in the crystal lattice. The different H-bonding lead to modulation of optical properties that was further supported highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) calculation. Further the stability calculation indicates that dimer (1 b) structure was more stable by 8.54 kcal/mole relative to catemer (1a) motifs. Further, the supramolecular interactions in catemer (1a) and dimer (1 b) motifs was studied by Hirshfeld surface and fingerprint plots to gain insight and compare the different functional groups contribution for intermolecular interactions in the polymorphic crystals which clearly showed different intermolecular interactions in polymorphs. [ABSTRACT FROM AUTHOR]