DOI QR코드

DOI QR Code

Fabrication of Spiropyran-functionalized Photochromic Hydrogel Lenses

  • Received : 2018.01.18
  • Accepted : 2018.02.19
  • Published : 2018.03.30

Abstract

Poly(hydroxyethyl methacrylate)-based hydrogels were surface-functionalized with spiropyran (SP) derivatives to obtain photochromic contact lenses. The contact lens reversibly changes from colorless to purple as response to UV light since colorless ring-closed SP state converts to purple ring-opened merocyanine (MC) state under UV light irradiation. The purple contact lens emits red light at 640 nm. Importantly, the presence of SP segments did not significantly affect the equilibrium water content (EWC) of the lens. SP-functionalized hydrogel lenses may find potential applications in developing light-adaptive ophthalmic materials.

Keywords

References

  1. S. Ashraf, H.-K. Park, H. Park, and S. H. Lee, "Snapshot of phase transition in thermoresponsive hydrogel PNIPAM: role in drug delivery and tissue engineering", Macromol. Res., Vol. 24, pp. 297-304, 2016. https://doi.org/10.1007/s13233-016-4052-2
  2. X. H. Hu, H. P. Tan, D. Li, and M. Y. Gu, "Surface functionalisation of contact lenses by CS/HA multilayer film to improve its properties and deliver drugs", Materials Technology, Vol. 29, pp. 8-13, 2014. https://doi.org/10.1179/1753555713Y.0000000063
  3. D. Lee, S. Cho, H. S. Park, and I. Kwon, "Ocular drug delivery through pHEMA-hydrogel contact lenses Co-loaded with lipophilic vitamins", Sci. Rep., Vol. 6, 2016.
  4. R. A. Kyle, D. P. Steensma, and M. A. Shampo, "Otto wichterle-inventor of the first soft contact lenses", Mayo Clin. Proc., Vol. 91, pp. e45-e46, 2016. https://doi.org/10.1016/j.mayocp.2016.01.016
  5. I. Tomatsu, K. Peng, and A. Kros, "Photoresponsive hydrogels for biomedical applications", Adv. drug Deliv. Rev., Vol. 63, pp. 1257-1266, 2011. https://doi.org/10.1016/j.addr.2011.06.009
  6. Y.-S. Nam, I. Yoo, O. Yarimaga, I. S. Park, D.-H. Park, S. Song, J.-M. Kim, and C. W. Lee, "Photochromic spiropyran-embedded PDMS for highly sensitive and tunable optochemical gas sensing", Chem. Commun., Vol. 50, pp. 4251-4254, 2014. https://doi.org/10.1039/C4CC00567H
  7. S. Scarmagnani, Z. Walsh, C. Slater, N. Alhashimy, B. Paull, M. Macka, and D. Diamond, "Polystyrene bead-based system for optical sensing using spiropyran photoswitches", J. Mater. Chem., Vol. 18, pp. 5063-5071, 2008. https://doi.org/10.1039/b810080b
  8. Y. Shiraishi, M. Itoh, and T. Hirai, "Thermal isomerization of spiropyran to merocyanine in aqueous media and its application to colorimetric temperature indication", Phys. Chem. Chem. Phys., Vol. 12, pp. 13737-13745, 2010. https://doi.org/10.1039/c0cp00140f
  9. J. Bonefacino, M. L. V. Tse, C. F. J. Pun, X. Cheng,W. K. E. Chan, A. Boersma, and H. Y. Tam, "Characterization of spirooxazine and spiropyran hosted in poly (methyl methacrylate) for germicidal UV source indicator application", Optics and Photonics Journal, Vol. 3, pp. 11-16, 2013.
  10. L. Baumann, K. Scholler, D. de Courten, D. Marti, M. Frenz, M. Wolf, R. M. Rossi, and L. J. Scherer, "Development of light-responsive porous polycarbonate membranes for controlled caffeine delivery", RSC Adv., Vol. 3, pp. 23317-23326, 2013. https://doi.org/10.1039/c3ra44399j
  11. B. Liao, P. Long, B. He, S. Yi, B. Ou, S. Shen, and J. Chen, "Reversible fluorescence modulation of spiropyran-functionalized carbon nanoparticles", J. Mater. Chem. C, Vol. 1, pp. 3716-7321, 2013. https://doi.org/10.1039/c3tc00906h
  12. J.-P. Jee and H.-J. Kim, "Development of hydrogel lenses with surface immobilized PEG layers to reduce protein adsorption", Bull. Korean Chem. Soc., Vol. 36, pp. 2682-2687, 2015. https://doi.org/10.1002/bkcs.10545
  13. M.-J. Lee and A. Sung, "Study on the preparation and characterization of ophthalmic polymer with high and low-water content", Journal of the Korean Chemical Society-Daehan Hwahak Hoe Jee, Vol. 61, pp. 346-351, 2017.
  14. M. Lira, L. Santos, J. Azeredo, E. Yebra-Pimentel, and M. E. C. D. R. Oliveira, "The effect of lens wear on refractive index of conventional hydrogel and silicone-hydrogel contact lenses: a comparative study", Cont. Lens Anterior Eye, Vol. 31, pp. 89-94, 2008. https://doi.org/10.1016/j.clae.2007.09.001
  15. L. Florea, D. Diamond, and F. Benito Lopez, "Photo-Responsive polymeric structures based on spiropyran", Macromol. Mater. Eng., Vol. 297, pp. 1148-1159, 2012. https://doi.org/10.1002/mame.201200306