Multihydroxy-anthraquinone derivatives as free radical and cationic photoinitiators of various photopolymerizations under Green LED

Jing Zhang, Nicholas S. Hill, Jacques Lalevée, Jean-Pierre Fouassier, Jiacheng Zhao, Bernadette Graff, Timothy W. Schmidt, Scott H. Kable, Martina H. Stenzel, Michelle L. Coote, Pu Xiao

Research output: Contribution to journal › Article › Research › peer-review

38 Citations (Scopus)

Abstract

Multihydroxy-anthraquinone derivatives [i.e., 1,2,4-trihydroxyanthraquinone (124-THAQ), 1,2,7-trihydroxyanthraquinone (127-THAQ), and 1,2,5,8-tetrahydroxyanthraquinone (1258-THAQ)] can interact with various additives [e.g., iodonium salt, tertiary amine, N-vinylcarbazole, and 2-(4-methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine] under household green LED irradiation to generate active species (cations and radicals). The relevant photochemical mechanism is investigated using quantum chemistry, fluorescence, cyclic voltammetry, laser flash photolysis, steady state photolysis, and electron spin resonance spin-trapping techniques. Furthermore, the multihydroxy-anthraquinone derivative-based photoinitiating systems are capable of initiating cationic photopolymerization of epoxides or divinyl ethers under green LED, and the relevant photoinitiation ability is consistent with the photochemical reactivity (i.e., 124-THAQ-based photoinitiating system exhibits highest reactivity and photoinitiation ability). More interestingly, multihydroxy-anthraquinone derivative-based photoinitiating systems can initiate free radical crosslinking or controlled (i.e., reversible addition−fragmentation chain transfer) photopolymerization of methacrylates under green LED. It reveals that multihydroxy-anthraquinone derivatives can be used as versatile photoinitiators for various types of photopolymerization reactions.

Original languageEnglish
Article number1800172
Number of pages6
JournalMacromolecular Rapid Communications
Volume39
Issue number19
DOIs
Publication statusPublished - Oct 2018
Externally publishedYes

Keywords

  • DFT calculations
  • green LED
  • multihydroxy-anthraquinone derivatives
  • photoinitiator
  • photopolymerization

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  • ARC Centre of Excellence in Exciton Science

    Mulvaney, P. (Primary Chief Investigator (PCI)), Ghiggino, K. P. (Chief Investigator (CI)), Smith, T. A. (Chief Investigator (CI)), Sader, J. E. (Chief Investigator (CI)), Wong, W. W. H. (Chief Investigator (CI)), Russo, S. (Chief Investigator (CI)), Cole, J. (Chief Investigator (CI)), Jasieniak, J. (Chief Investigator (CI)), Funston, A. (Chief Investigator (CI)), Bach, U. (Chief Investigator (CI)), Cheng, Y. (Chief Investigator (CI)), Lakhwani, G. (Chief Investigator (CI)), Widmer-Cooper, A. (Chief Investigator (CI)), McCamey, D. (Chief Investigator (CI)), Schmidt, T. (Chief Investigator (CI)), Gomez, D. E. (Partner Investigator (PI)), Scholes, F. (Partner Investigator (PI)), McCallum, R. (Partner Investigator (PI)), Dicinoski, G. (Partner Investigator (PI)), Du, C. (Partner Investigator (PI)), Plenio, M. B. (Partner Investigator (PI)), Tiang, J. (Partner Investigator (PI)), Neaton, J. (Partner Investigator (PI)), Lippitz, M. (Partner Investigator (PI)) & Hao, X. (Partner Investigator (PI))

    Monash University – Internal School Contribution, Monash University – Internal Faculty Contribution, Monash University – Internal Department Contribution, Monash University – Internal University Contribution

    30/06/17 → 30/06/24

    Project: Research

  • ARC Centre of Excellence for Electromaterials Science

    Wallace, G. G. (Primary Chief Investigator (PCI)), Forsyth, M. (Chief Investigator (CI)), Macfarlane, D. (Chief Investigator (CI)), Officer, D. (Chief Investigator (CI)), Cook, M. J. (Chief Investigator (CI)), Dodds, S. (Chief Investigator (CI)), Spinks, G. (Chief Investigator (CI)), Alici, G. (Chief Investigator (CI)), Moulton, S. (Chief Investigator (CI)), in het Panhuis, M. (Chief Investigator (CI)), Kapsa, R. M. I. (Chief Investigator (CI)), Higgins, M. (Chief Investigator (CI)), Mozer, A. (Chief Investigator (CI)), Crook, J. (Chief Investigator (CI)), Innis, P. (Chief Investigator (CI)), Coote, M. L. (Chief Investigator (CI)), Wang, X. (Chief Investigator (CI)), Howlett, P. C. (Chief Investigator (CI)), Pringle, J. (Chief Investigator (CI)), Hancock, L. (Chief Investigator (CI)), Paull, B. (Chief Investigator (CI)), Sparrow, R. (Chief Investigator (CI)), Zhang, J. (Chief Investigator (CI)), Spiccia, L. (Chief Investigator (CI)), Diamond, D. (Partner Investigator (PI)), Guldi, D. (Partner Investigator (PI)), Kim, S. J. (Partner Investigator (PI)), Unwin, P. (Partner Investigator (PI)) & Watanabe, M. (Partner Investigator (PI))

    Australian Research Council (ARC)

    30/06/14 → 30/06/21

    Project: Research

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