Fluorescent Covalently Cross-Linked Cellulose Networks via Light-Induced Ligation

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A facile light-induced procedure for the covalent cross-linking of cellulose at ambient conditions employing the nitrile imine mediated tetrazole-ene cycloaddition (NITEC) reaction is presented. Cellulose-tetrazoles with 2 degrees of substitution (0.14 and 0.23) were synthesized in a solution-based transesterification procedure in an ionic liquid. Two bismaleimides with either a trioxatridecane or a dithiodipropionyl backbone were used as cross-linkers to form fluorescent, covalently cross-linked cellulose networks and films, which were characterized by UV/vis spectroscopy, fluorescence spectroscopy, DSC, and TGA. The films showed a broad emission band from 500-700 nm and were thermally stable up to 200 °C. Using the bismaleimide with a disulfide moiety as the cross-linker, reductive degradation of the films can be induced. Finally, cellulose-tetrazole was cross-linked in a spatially resolved fashion, providing a strategy for the shaping of films based on renewable resources.