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A solvent-less and additive-free approach was developed for the cross-linking of π-conjugated polymers through the formation of polydiacetylene (PDA) cross-links. Different ratios of conjugation-breaking spacers incorporating 1,3-butadiyne motifs were inserted into semicrystalline diketopyrrolopyrrole-based polymers and reacted under UV light to trigger a topochemical photopolymerization. Upon photo-cross-linking, the formation of PDA cross-links was confirmed by Raman spectroscopy, and the resulting materials were further characterized through various techniques including Fourier transform infrared spectroscopy, atomic force microscopy, X-ray scattering, and UV–vis spectroscopy to evaluate their photophysical and optical properties. Furthermore, the mechanical properties of the PDA-containing semiconducting materials were evaluated via quantitative nanomechanical mapping, which confirmed that an …