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Polymorphism is an interesting phenomenon critical to our understanding of structure–property relationships in solid-state functional materials. We report the synthesis and structural characterization of two polymorphic forms of a DPP-Boc derivative, DPP4T-α and DPP4T-β, as well as the study of their optical properties. Thin film studies have been carried out to identify the specific polymorphic form that exists in contact with the substrate and also to obtain a better understanding of the interface morphology with respect to crystal packing. The two polymorphs, DPP4T-α and DPP4T-β, have been structurally characterized using single crystal/powder X-ray diffraction data with a detailed analysis of Hirshfeld surfaces and fingerprint plots facilitating a comparison of the type and nature of intermolecular interactions in the supramolecular architectures. DPP4T-α crystallizing in a space group P2₁/c with Z′ = 0.5 interlinked …