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Photoresponsive polyesters by incorporation of alkoxyphenacyl or coumarin chromophores along the backbone

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Abstract

The synthesis and photochemical characterization of two classes of photoresponsive polyesters are described. These polyesters contain either alkoxyphenacyl or coumarin chromophores embedded along the polymer chain. The alkoxyphenacyl polyesters undergo efficient photoinduced chain scission upon irradiation at 300 nm in solution or as a nanoparticle suspension. At 254 nm the coumarin polyesters undergo polymer chain scission. Irradiation of the coumarin polyesters in solution at 350 nm results in both chain crosslinking and chain scission behavior, while irradiation of the coumarin polyesters as nanoparticles results in chain crosslinking. The properties of the alkoxyphenacyl and coumarin polyesters are influenced by the choice of diacid as seen from their thermal behavior. The use of glutamic acid enabled surface or bulk functionalization of the photoresponsive polymers. In addition, controlled release of Nile Red from coumarin polyester nanoparticles is demonstrated by modulation of the wavelength and intensity of irradiation.

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References

  1. X. Y. Huang, S. Y. Han, W. Huang and X. G. Liu, Chem. Soc. Rev. 2013, 42, 173.

    Article  CAS  Google Scholar 

  2. M. Oellerich, J. Clin. Chem. Clin. Biochem. 1984, 22, 895.

    CAS  PubMed  Google Scholar 

  3. S. Banfi, E. Caruso, S. Caprioli, L. Mazzagatti, G. Canti, R. Ravizza, M. Gariboldi and E. Monti, Bioorg. Med. Chem. 2004, 12, 4853.

    Article  CAS  Google Scholar 

  4. M. Irie, Pure Appl. Chem. 1990, 62, 1495.

    Article  CAS  Google Scholar 

  5. K. M. Lee, M. L. Smith, H. Koerner, N. Tabiryan, R. A. Vaia, T. J. Bunning and T. J. White, Adv. Funct. Mater. 2011, 21, 2913.

    Article  CAS  Google Scholar 

  6. T. Shimoboji, E. Larenas, T. Fowler, S. Kulkarni, A. S. Hoffman and P. S. Stayton, Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 16592.

    Article  CAS  Google Scholar 

  7. Y. L. Yu, M. Nakano and T. Ikeda, Nature 2003, 425, 145.

    Article  CAS  Google Scholar 

  8. A. Lendlein, H. Y. Jiang, O. Junger and R. Langer, Nature 2005, 434, 879.

    Article  CAS  Google Scholar 

  9. E. Kim, Y. K. Choi and M. H. Lee, Macromolecules 1999, 32, 4855.

    Article  CAS  Google Scholar 

  10. C. K. Lee, D. A. Davis, S. R. White, J. S. Moore, N. R. Sottos and P. V. Braun, J. Am. Chem. Soc. 2010, 132, 16107.

    Article  CAS  Google Scholar 

  11. R. Tong, H. D. Hemmati, R. Langer and D. S. Kohane, J. Am. Chem. Soc. 2012, 134, 8848.

    Article  CAS  Google Scholar 

  12. G. D. Fu, L. Q. Xu, F. Yao, G. L. Li and E. T. Kang, Acs Appl. Mater. Interfaces 2009, 1, 2424.

    Article  CAS  Google Scholar 

  13. A. P. Esser-Kahn, S. A. Odom, N. R. Sottos, S. R. White and J. S. Moore, Macromolecules 2011, 44, 5539.

    Article  CAS  Google Scholar 

  14. D. Q. Liu, C. W. M. Bastiaansen, J. M. J. den Toonder and D. J. Broer, Macromolecules 2012, 45, 8005.

    Article  CAS  Google Scholar 

  15. I. Tomatsu, K. Peng and A. Kros, Adv. Drug Delivery Rev. 2011, 63, 1257.

    Article  CAS  Google Scholar 

  16. Q. Yan, D. Han and Y. Zhao, Polym. Chem. 2013, 4, 5026.

    Article  CAS  Google Scholar 

  17. S. Deshayes and A. M. Kasko, J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3531.

    Article  CAS  Google Scholar 

  18. N. Fomina, J. Sankaranarayanan and A. Almutairi, Adv. Drug Delivery Rev. 2012, 64, 1005.

    Article  CAS  Google Scholar 

  19. A. M. Kloxin, A. M. Kasko, C. N. Salinas and K. S. Anseth, Science 2009, 324, 59.

    Article  CAS  Google Scholar 

  20. D. H. Han, X. Tong and Y. Zhao, Macromolecules 2011, 44, 437.

    Article  CAS  Google Scholar 

  21. G. Pasparakis, T. Manouras, P. Argitis and M. Vamvakaki, Macromol. Rapid Commun 2012, 33, 183.

    Article  CAS  Google Scholar 

  22. S. Sun, A. C. Elaheh and A. Joy, ACS Macro Lett. 2012, 1, 1184.

    Article  CAS  Google Scholar 

  23. R. S. Givens, D. Heger, B. Hellrung, Y. Kamdzhilov, M. Mac, P. G. Conrad, E. Cope, J. I. Lee, J. F. Mata-Segreda, R. L. Schowen and J. Wirz, J. Am. Chem. Soc. 2008, 130, 3307.

    Article  CAS  Google Scholar 

  24. V. S. N. M. Maddipatla, D. Wehrung, C. Tang, W. Fan, M. O. Oyewumi, T. Miyoshi and A. Joy, Macromolecules 2013, 46, 5133.

    Article  CAS  Google Scholar 

  25. B. D. Ulery, L. S. Nair and C. T. Laurencin, J. Polym. Sci., Part B: Polym. Phys. 2011, 49, 832.

    Article  CAS  Google Scholar 

  26. K. Whitaker-Brothers and K. Uhrich, J. Biomed. Mater. Res., Part A 2004, 70, 309.

    Article  Google Scholar 

  27. Q. L. Chu, M. M. Brahmi, A. Solovyev, S. H. Ueng, D. Curran, M. Malacria, L. Fensterbank and E. Lacote, Chem.–Eur. J. 2009, 15, 12937.

    Article  CAS  Google Scholar 

  28. R. M. Moriarty, B. A. Berglund and R. Penmasta, Tetrahedron Lett. 1992, 33, 6065.

    Article  CAS  Google Scholar 

  29. S. Gokhale, Y. Xu and A. Joy, Biomacromolecules 2013, 14, 2489.

    Article  CAS  Google Scholar 

  30. B. Ewa, W. Maciej, S. Marcin, D. Grzegorz, Z. Michal, P. Jan and O. Jozef, Bioorg. Med. Chem. Lett. 2012, 22, 5574.

    Article  Google Scholar 

  31. P. Klan, T. Solomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov and J. Wirz, Chem. Rev. 2013, 113, 119.

    Article  CAS  Google Scholar 

  32. R. S. Givens and J.-I. Lee, J. Photosci. 2003, 10, 37.

    CAS  Google Scholar 

  33. T. Furuta, S. S. H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk and R. Y. Tsien, Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1193.

    Article  CAS  Google Scholar 

  34. A. P. Pelliccioli and J. Wirz, Photochem. Photobiol. Sci. 2002, 1, 441.

    Article  Google Scholar 

  35. N. Ramasubbu, K. Gnanaguru, K. Venkatesan and V. Ramamurthy, Can. J. Chem. 1982, 60, 2159.

    Article  CAS  Google Scholar 

  36. K. Gnanaguru, N. Ramasubbu, K. Venkatesan and V. Ramamurthy, J. Org. Chem. 1985, 50, 2337.

    Article  CAS  Google Scholar 

  37. L. H. Leenders, E. Schouteden and F. C. De Schryver, J. Org. Chem. 1973, 38, 957.

    Article  CAS  Google Scholar 

  38. Y. Zhao, L. Tremblay and Y. Zhao, Macromolecules 2011, 44, 4007.

    Article  CAS  Google Scholar 

  39. V. Hagen, J. Bendig, S. Frings, T. Eckardt, S. Helm, D. Reuter and U. B. Kaupp, Angew. Chem., Int. Ed. 2001, 40, 1045.

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Polymer Science, The University of Akron, Akron, Ohio, 44325, USA

    Elaheh A. Chamsaz, Shuangyi Sun, Murthy V. S. N. Maddipatla & Abraham Joy

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  1. Elaheh A. Chamsaz
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  2. Shuangyi Sun
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  3. Murthy V. S. N. Maddipatla
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  4. Abraham Joy
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Correspondence to Abraham Joy.

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Chamsaz, E.A., Sun, S., Maddipatla, M.V.S.N. et al. Photoresponsive polyesters by incorporation of alkoxyphenacyl or coumarin chromophores along the backbone. Photochem Photobiol Sci 13, 412–421 (2014). https://doi.org/10.1039/c3pp50311a

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