Conjugated Polymer with Polydiacetylene Cross-Links Through Topochemical Polymerization of 1,3-Butadiyne Moieties Toward Photopatternable Thin Films AITranslate

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DOI：https://doi.org/10.1021/acsapm.9b00520

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A new methodology to covalently cross-link π-conjugated polymers by generating π-conjugated bridges was developed through the topochemical polymerization of 1,3-butadiyne moieties. Isoindigo-based oligomers containing 1,3-butadiyne were prepared and amide moieties were incorporated to enable hydrogen bonding which promoted an optimal morphology for cross-linking through 1,4-addition. Moreover, the molecular weight of the semiconducting materials was carefully controlled to promote crystallinity, leading to the formation of a nanofibrillar network. Upon formation of polydiacetylene cross-links, the resulting conjugated polymeric network was characterized using grazing incidence X-ray diffraction, Raman spectroscopy, atomic force microscopy, and optical spectroscopy. Furthermore, transient absorption and fluorescence spectroscopy were used to probe for the effect of the new π-conjugated cross-links on photophysical properties. The new π-conjugated bridges were shown to maintain the morphology and the photophysical properties while altering other important properties for polymer processing, such as the solubility. This new, mild, and additive-free photo-cross-linking approach is particularly promising for the patterning and processing of π-conjugated materials and the rigidification of conjugated polymeric network, thus creating new opportunities for the processing of organic semiconductors and fabrication of organic electronic devices.