Incorporation of 5-hydroxyindazole into the self-polymerization of dopamine for novel polymer synthesis

Matthew B. Peterson, Solomon P. Le-Masurier, Khoon Lim, James M. Hook, Penny Martens, Anthony M. Granville*

*Corresponding author for this work

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Investigation into the mussel-inspired polymerization of dopamine has led to the realization that other compounds possessing potential quinone structures could undergo similar self-polymerizations in mild buffered aqueous conditions. To this end, 5-hydroxyindazole was added to a dopamine polymerization matrix in varying amounts, to study its incorporation into a polydopamine coating of silica particles. Solid-state 13C NMR spectroscopy confirmed the presence of the indazole in the polymer shell when coated onto silica gel. SEM and DLS analysis also confirmed that the presence of the indazole in the reaction matrix yielded monodisperse polymer-coated particles, which retained their polymer shell upon HF etching, except when high levels of the indazole were used. Characterization data and examination of incorporation mechanism suggests that the 5-hydroxyindazole performs the function of a chain-terminating agent. Cytotoxicity studies of the polymer particles containing 5-hydroxyindazole showed dramatically lower toxicity levels compared to polydopamine alone. The self-polymerization of dopamine is extended to incorporate 5-hydroxyindazole into the polymerization system. The structurally similar indazole can oxidatively couple in the same fashion as dopamine, proof that the polymerization reaction is expandable to other materials for new green chemistry reactions.

Original languageEnglish
Pages (from-to)291-297
Number of pages7
JournalMacromolecular Rapid Communications
Volume35
Issue number3
DOIs
Publication statusPublished - Feb 2014
Externally publishedYes

Keywords

  • 5-hydroxyindazole
  • cytotoxicity
  • dopamine
  • polymerization
  • self-polymerization

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    Peterson, M. B., Le-Masurier, S. P., Lim, K., Hook, J. M., Martens, P., & Granville, A. M. (2014). Incorporation of 5-hydroxyindazole into the self-polymerization of dopamine for novel polymer synthesis. Macromolecular Rapid Communications, 35(3), 291-297. https://doi.org/10.1002/marc.201300746