Citation: Ming-Hui He, Rui-Xin Xu, Guang-Xue Chen, Zhao-Hua Zeng, Jian-Wen Yang. A thioxanthone-based photocaged superbase for highly effective free radical photopolymerization[J]. Chinese Chemical Letters, ;2014, 25(11): 1445-1448. doi: 10.1016/j.cclet.2014.05.031 shu

A thioxanthone-based photocaged superbase for highly effective free radical photopolymerization

  • Corresponding author: Jian-Wen Yang, 
  • Received Date: 11 February 2014
    Available Online: 14 May 2014

    Fund Project: This research was financially supported by National Natural Science Foundation of China (No. 20974127, 21374135) (No. 20974127, 21374135) China Postdoctoral Science Foundation (No. 2013M542178) (No. 2013M542178) and the Fundamental Research Funds for the Central Universities (No. 2013ZB0025). (No. C713043z)

  • Thioxanthone-based N-phthalimidoamino acid ammonium salt (thioxanthen-DBU) as a photocaged base was synthesized and characterized. The photochemical properties and initiation mechanism were analyzed. It was found that the compound absorbs over the UV and visible region with relatively high absorption coefficients. Furthermore, the covalent binding of N-phthalimidoamino acid and type Ⅱ chromophores (thioxanthone, TX) remarkably improved the photoreactivity. Specifically, in combination with a benzoyl peroxide initiator, thioxanthen-DBU was able to initiate the amine-mediated redox photopolymerization of trimethylol propane triacrylate (TMPTA), and an excellent photopolymerization profile was obtained.
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    1. [1]

      [1] Y. Yagci, S. Jockusch, N.J. Turro, Photoinitiated polymerization: advances, challenges, and opportunities, Macromolecules 43 (2010) 6245-6260.

    2. [2]

      [2] L. Gonsalvi, M. Peruzzini, Novel synthetic pathways for bis (acyl) phosphine oxide photoinitiators, Angew. Chem. Int. Ed. 51 (2012) 7895-7897.

    3. [3]

      [3] J.V. Crivello, E. Reichmanis, Photopolymer materials and processes for advanced technologies, Chem. Mater. 26 (2014) 533-548.

    4. [4]

      [4] Y.L. Xu, H.J. Xu, X.S. Jiang, J. Yin, Versatile functionalization of the micropatterned hydrogel of hyperbranched poly(ether amine) based on "thiol-yne" chemistry, Adv. Funct. Mater. 24 (2014) 1679-1686.

    5. [5]

      [5] M. Tehfe, F.E.D.E. Dumur, P. Xiao, et al., Chalcone derivatives as highly versatile photoinitiators for radical, cationic, thiol-ene and IPN polymerization reactions upon exposure to visible light, Polym. Chem. 5 (2014) 382-390.

    6. [6]

      [6] J.L. Yang, S.Q. Shi, F. Xu, J. Nie, Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator, Photochem. Photobiol. Sci. 12 (2013) 323-329.

    7. [7]

      [7] H. Tar, D. Sevinc Esen, M. Aydin, et al., Panchromatic type Ⅱ photoinitiator for free radical polymerization based on thioxanthone derivative, Macromolecules 46 (2013) 3266-3272.

    8. [8]

      [8] H. Chen, Z.L. Zou, S.L. Tan, et al., Efficient synthesis of water-soluble calix[4]arenes via thiol-ene "click" chemistry, Chin. Chem. Lett. 24 (2013) 367-369.

    9. [9]

      [9] Y.Y. Cui, Y.E. Ren, X.X. Liu, Synthesis of methyl methacrylate star-branched polymer with divinylbenzene as a linking agent via controlled/living photopolymerization, Chin. Chem. Lett. 23 (2012) 985-988.

    10. [10]

      [10] M.H. He, X. Huang, Y.G. Huang, Z.H. Zeng, J.W. Yang, Photoinduced redox initiation for fast polymerization of acrylaytes based on latent superbase and peroxides, Polymer 53 (2012) 3172-3177.

    11. [11]

      [11] M.H. He, X. Huang, Z.H. Zeng, J.W. Yang, Photo-triggered redox frontal polymerization: a new tool for synthesizing thermally sensitive materials, J. Polym. Sci. A: Polym. Chem. 51 (2013) 4515-4521.

    12. [12]

      [12] M.H. He, X. Huang, Z.H. Zeng, J.W. Yang, Phototriggered base proliferation: a highly efficient domino reaction for creating functionally photo-screened materials, Macromolecules 46 (2013) 6402-6407.

    13. [13]

      [13] M.H. He, S. Jiang, R.X. Xu, et al., Domino free radical photopolymerization based on phototriggered base proliferation reaction and redox initiation, J. Polym. Sci. A: Polym. Chem. 52 (2014) 1560-1569.

    14. [14]

      [14] G. Yilmaz, B. Aydogan, G. Temel, et al., Thioxanthone-fluorenes as visible light photoinitiators for free radical polymerization, Macromolecules 43 (2010) 4520- 4526.

    15. [15]

      [15] D.K. Balta, G. Temel, G. Goksu, et al., Thioxanthone-diphenyl anthracene: visible light photoinitiator, Macromolecules 45 (2011) 119-125.

    16. [16]

      [16] D. Tunc, Y. Yagci, Thioxanthone-ethylcarbazole as a soluble visible light photoinitiator for free radical and free radical promoted cationic polymerizations, Polym. Chem. 2 (2011) 2557-2563.

    17. [17]

      [17] G. Yilmaz, S. Beyazit, Y. Yagci, Visible light induced free radical promoted cationic polymerization using thioxanthone derivatives, J. Polym. Sci. A: Polym. Chem. 49 (2011) 1591-1596.

    18. [18]

      [18] M.A. Tehfe, F. Dumur, B. Graff, et al., Design of new Type I and Type Ⅱ photoinitiators possessing highly coupled pyrene-ketone moieties, Polym. Chem. 4 (2013) 2313-2324.

    19. [19]

      [19] H.Y. Wang, J. Wei, X.S. Jiang, J. Yin, Highly efficient, polymerizable, sulfur-containing photoinitiator comprising a structure of planar N-phenylmaleimide and benzophenone for photopolymerization, J. Polym. Sci. A: Polym. Chem. 44 (2006) 3738-3750.

    20. [20]

      [20] H. Wang, J. Wei, X. Jiang, et al., Novel chemical-bonded polymerizable sulfurcontaining photoinitiators comprising the structure of planar N-phenylmaleimide and benzophenone for photopolymerization, Polymer 47 (2006) 4967- 4975.

    21. [21]

      [21] S.K. Dogruyol, Z. Dogruyol, N. Arsu, A thioxanthone-based visible photoinitiator, J. Polym. Sci. A: Polym. Chem. 49 (2011) 4037-4043.

    22. [22]

      [22] W. Fischer, Aromatic nucleophilic substitution. Part 3. Preparation of novel 9-oxo- 9H-thioxanthene-and 9-oxo-9H-xanthenedicarboximides and-dicarboxylates, Helv. Chim. Acta 74 (1991) 1119-1126.

    23. [23]

      [23] C.W. Miller, E.S. Jö nsson, C.E. Hoyle, K. Viswanathan, E.J. Valente, Evaluation of Naromatic maleimides as free radical photoinitiators: a photophysical and photopolymerization characterization, J. Phys. Chem. A 105 (2001) 2707-2717.

    24. [24]

      [24] Y. Takahashi, T. Miyashi, U.C. Yoon, et al., Mechanistic studies of the azomethine ylide-forming photoreactions of N-(silylmethyl) phthalimides and N-phthaloylglycine, J. Am. Chem. Soc. 121 (1999) 3926-3932.

    25. [25]

      [25] H.G.O. Rner, A.G. Griesbeck, T. Heinrich, et al., Time-resolved spectroscopy of sulfur-and carboxy-substituted N-alkylphthalimides, Chem. Eur. J. 7 (2001) 1530-1538.

    26. [26]

      [26] M. Aydin, N. Arsu, Y. Yagci, S. Jockusch, N.J. Turro, Mechanistic study of photoinitiated free radical polymerization using thioxanthone thioacetic acid as onecomponent type Ⅱ photoinitiator, Macromolecules 38 (2005) 4133-4138.

    27. [27]

      [27] M. Aydin, N. Arsu, Y. Yagci, One-component bimolecular photoinitiating systems, 2, Macromol. Rapid Commun. 24 (2003) 718-723.

    28. [28]

      [28] D.K. Balta, G. Temel, M. Aydin, N. Arsu, Thioxanthone based water-soluble photoinitiators for acrylamide photopolymerization, Eur. Polym. J. 46 (2010) 1374-1379.

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