Photochromic Materials


CSIRO has developed an extensive capability in the synthesis of photochromic dyes and in methods of controlling their switching speeds in polymer matrices. Key achievements in our research are:

  • The development of fast fade of photochromic dyes in polymer matrices  with 4 generations of photochromic dye-polymer conjugates invented.
  • The development of a method of synchronizing photochromic dyes in polymer matrices. This allows enormous flexibility in formulating new products.
  • The use of living radical polymerization methods to dial-up switching speeds of photochromic dye in polymers.
  • The use of photochromic dyes as optical probes for micelle assembly.
  • Independent synthesis of major commercial classes of naphthopyran and spirooxazine dyes by Transitions, Rodenstock, Vivimed (formerly James Robinson), Tokuyama and Visionease.
  • Analysis and identification of major components of key commercial photochromic lens formulations of Transitions, Rodenstock, Vision-ease.
  • Synthesis of the first true red spirooxazine.
  • Development of a practical synthesis of green spirooxazine.
  • Optimization of dye synthesis and flow synthesis of dyes to minimize waste production and increase yields.
  • Development of a method of making spiropryans responsive to CO2 as a stimuli or as CO2 detectors.
  • Extensive academic publication record in high impact journals.

This work is all part of CSIRO’s general capability in light responsive systems.

Research Team:

Led by Richard Evans.  Key members that contributed to the work listed above are available. Our core team is strong in organic synthesis, polymer synthesis and polymer conjugation. We can perform kinetic analyses of the dyes in solution and in polymer substrates.

Publications in Photochromism.

  1. Tunable photodynamic switching of DArE@PAF-1 for carbon capture. Lydon, R., Konstas, K., Evans. R.A., Keddie, D.J., Hill, M.R., Ladewig, B.P., Advanced Functional Materials, 2015, 25, 4405-4411.
  2. Preparation and photochromic performance characterisitics of polyester-napthopyran conjugates in a rigid host matrix. Malic, N., Dagley, I.J., Evans, R.A. Dyes and Pigments, 2013, 97, 162—167. DOI:1016/j.dyepig.2012.12.021
  3. The use of poly(alkylene oxide)s to achieve fast and controlled photochormic switching in rigid matrices. Malic, N. , Evans, R.A., Journal of Polymer Science Part A: Polymer Chemistry. 2012, 50(7) 1434-1444, DOI: 10.1002/pola.25912
  4. Alkylation of Spiropyran Moiety Provides Reversible Photocontrol over Nanostructured Soft Materials. Fong, W-K., Malic, N., Evans, R. A. Hawley, A., Boyd, B., Hanley, T. Biointerfaces 2012 7 (3) DOI  1007/s13758-011-0003-9.
  5. A Molecular Canary: Spiropyran-Amidine as a Visual Probe for Carbon Dioxide Gas. Darwish, T.A., Evans, R.A., James, M., Malic, N., Triani, G., Hanley, T.L. Chemistry: A European Journal. 2011, 17, 11399-11404  doi: 10.1002/chem.201101723.
  6. Fast Switching Immobilized Photochromic Dyes. Malic, N., Campbell, J.A., Ali, A.S., Francis, C.L., Evans, R.A. Journal of Polymer Science, Polymer Chemistry, 2011, 49, 476-486.
  7. The application of a photochromic probe to monitor the self-assembly of thermosensitive block copolymers. Ercole, F., Malic, N., Simon Harrisson,  Davis,P., and Evans, R.A Soft Matter. 2011, 7, 2687–2696, doi: 10.1039/C0SM00746C.
  8. Controlling Molecular Mobility in Polymer Matrices: Synchronizing Switching Speeds of Multiple Photochromic Dyes.  Malic, N., Campbell, J.A., Ali, A.S., York, M., D’Souza, A., Evans, R.A. Macromolecules. 2010, 43, 8488-8501. DOI: 10.101051m
  9. CO2 Triggering and Controlling Orthogonally Multi-responsive Photochromic Systems. Darwish, T.A., Evans, R.A., James, M., Malic, N., Triani, G., Hanley, T.L. Journal of the American Chemical Society. 2010, 132, 10748-10755DOI: 1021/ja1013322
  10. Optimised Synthesis of 6’-Arylamino (Green) Photochromic Spirooxazines. Evans R.A. and York, M. Synthetic Communications. 2010,40, 3618-3628.
  11. Photo-responsive systems: photochromic polymers, light tiggered self assembly, surface modification fluorescence modulation and beyond. Ercole, F, Davis, T.P, Evans R.A. Polymer Chemistry. 2010, 1, 37-54. DOI:10.1039/b9py00300b  Nov 2009.  Invited lead review for the launch of the new RSC Journal “Polymer Chemistry” and Cover Image for first edition.
  12. Synthesis and properties of 1,3,3-trimethylspiro[indoline-2,30-naphtho[2,1-b]
  13. [1,4]oxazin]-60-amine, a novel, red colouring photochromic spirooxazine. York, M., Evans, R.A. Tetrahedron letters, 2010, 51, 2195-2197  doi:10.1016/j.tetlet.2010.02.105.
  14. Photochromic spirooxazines functionalized with oligomers: investigation of core – oligomer interactions and photomerocyanine isomer interconversion using NMR spectroscopy and DFT. Yee, L,H., Hanley, T., Evans, R.A., Davis, T.P., Ball, G.E. Journal of Organic Chemistry. 2010, 75, 2851-2860. DOI: 10.1021/jo100081g.
  15. Photochromic Polymer Conjugates: The Importance of Macromolecular Architecture in Controlling Switching Speed within a Polymer Matrix.. Ercole, F., Malic, N., Simon Harrisson,  Davis,P., and Evans, R.A, Macromolecules, 2010, 43(1), 249-261. DOI: 1021/ma901830b
  16. Optimizing the photochromic performance of napthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation. Ercole, F., Malic, N., Davis,P., and Evans, R.A. Journal of Materials Chemistry, 2009 , 19, 5612-5623. DOI: 10.1039/B904345D
  17. Comprehensive Modulation of Rigid Methacrylate Napthopyran Polymers Ercole, F., Evans R.A., Davis, T.P. Macromolecules 2009, 42, 1500-1511
  18. Superior Photochromic Performance of Naphthopyrans in a Rigid Host Matrix Using Polymer Conjugation. Fast Dark and Tuneable. Malic, N. Campbell, J.A., Evans, R.A.  Macromolecules. 2008, 41, 1206-1214
  19. The Use of Block Copolymers to Systematically Modify Photochromic Behaviour. Such, G.K., Evans, R.A., Davis, T.P, Macromolecules , 2006, 39, 9562-9570.
  20. Rapid Photochromic Switching in a Rigid Polymer Matrix using Living Radical Polymerisation (ATRP), Such, G.K., Evans, R.A., Davis, T.P, Macromolecules , 2006, 39, 1391-1396.
  21. Research trends in photochromism: Control of Photochromism in Rigid Polymer Matrices and other Advances. Evans, R.A; Such, G.K. Australian Journal of Chemistry, 2005, 58, 825-830.  and Cover Image.
  22. The Generic Enhancement of Photochromic Dye SwitchingSpeeds in Rigid Polymer Matrices. Evans, R.A., Hanley, T.L., Skidmore, M.A., Davis, T.P., Such, G.K., Yee, L.H., Ball, G.E., Lewis, D.A. Nature Materials.  2005 , 4, 294-253 This describes a solution to the long standing problem of increasing photochromic dyes switching speeds in rigid polymer matrices. Commentaries on the article have featured in Science (Editors choice of Highlights from the recent literature 4th March  2005 p 1379) and Nature Materials (News and Views March 2005 p193-194).
  23. Tailoring Photochromic Perfomance of Polymer-Dye Conjugates Using Living Radical Polymerization (ATRP). Such, G.K., Evans, R.A., Davis, T.P. Cryst. Mol. Cryst. 2005, 430, 273-279.
  24. Control of Photochromism through Local Environment Effects using Living Radical Polymerisation, Such, G., Evans, R.A. and Davis, T.P. Macromolecules, 2004, 37, 9664-9666.
  25. Factors Influencing Photochromism of Spiro – compounds with Polymeric Matrices. Such, G. Evans, R.A., Yee, L.H., Davis, T.P. Journal of Macromolecular Science Part C Polymer Reviews, 2003, C43, 547