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One-pot one-step synthesis of a photo-cleavable cross-linker via Passerini reaction for fabrication of responsive polymeric particles

Polymer Bulletin volume 76, pages 1471–1487 (2019)Cite this article

Abstract

A new approach for the synthesis of a photo-cleavable cross-linker and preparation of light-responsive polymeric particles is proposed in the current work. A multicomponent reaction, Passerini reaction, is employed as a one-pot one-step synthetic approach for the preparation of the acrylate-based cross-linker (hexane-1,6-diylbis(azanediyl))bis(1-(2-nitrophenyl)-2-oxoethane-2,1-diyl) diacrylate) (PCDA). Briefly, Passerini reaction of 1,6-diisocyanohexane, 2-nitrobenzaldehyde and acrylic acid yields the photo-cleavable diacrylate with o-nitrobenzyl ester moieties. Subsequently, the cross-linker is successfully utilized in the preparation of poly(methyl methacrylate) microspheres and nanospheres via suspension and miniemulsion polymerization, respectively. Finally, light-induced degradations of the polymeric particles are conducted under UV light illumination (around 366 nm). All compounds and products in each step are well characterized by FTIR, 1H-NMR, UV–Vis spectroscopy, light microscopy and SEM.

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Acknowledgements

This study was financially supported by Yildiz Technical University (Project#: 2013-07-04-KAP05).

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Author notes

  1. Muhammet U. Kahveci

    Present address: Department of Chemistry, Faculty of Science and Letters, Istanbul Technical University, 34467, Maslak, Sariyer, Istanbul, Turkey

Authors and Affiliations

  1. Department of Bioengineering, Faculty of Chemical and Metallurgical Engineering, Davutpasa Campus, Yildiz Technical University, 34210, Esenler, Istanbul, Turkey

    Gozde Deveci & Muhammet U. Kahveci

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  1. Gozde Deveci
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Correspondence to Muhammet U. Kahveci.

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Deveci, G., Kahveci, M.U. One-pot one-step synthesis of a photo-cleavable cross-linker via Passerini reaction for fabrication of responsive polymeric particles. Polym. Bull. 76, 1471–1487 (2019). https://doi.org/10.1007/s00289-018-2449-0

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