Photochromism of Naphthopyrans Possessing a Spirophenanthrene Unit and the Ophthalmic Lens Comprising of Them

  • Junji Momoda
  • Yasushi Yokoyama


In this chapter, the photochromic properties of naphthopyrans applicable to plastic photochromic lenses are described. In particular, introduction of electron-donating groups on the skeleton of a naphthopyran, 3,3-diphenyspiro[benzofluorenopyran-cyclopentaphenanthrene], and their effects are discussed in detail. Introduction of a methoxy group to C6 caused the bathochromic shift of the absorption band of the MC form. Further introduction of methoxy groups to the para-position of the phenyl groups on C3 induced faster decoloration of the MC form. Additional introduction of a methoxy group to C11 increased the absorbance. These naphthopyrans, however, showed poor photochromic properties in a solid matrix compared with those in solution. The matrix design of the plastic photochromic lenses to make the most of the potential property of naphthopyrans as well as to maintain the required properties as ophthalmic lenses is also described.


Photochromism Naphthopyran Ophthalmic lenses Phenanthrene Substituent effect 



We are heartily grateful to the co-workers of Tokuyama Corp. for supporting this work.


  1. 1.
    Van Gemert B, Kumar A, Knowles DB (1997) Naphthopyrans. Structural features and photochromic properties. Mol Cryst Liq Cryst 297:131–138CrossRefGoogle Scholar
  2. 2.
    Van Gemert B (2000) The commercialization of plastic photochromic lenses: a tribute to John Crano. Mol Cryst Liq Cryst 344:57–62CrossRefGoogle Scholar
  3. 3.
    Delbaere S, Luccioni-Houze B, Bochu C, Teral Y, Campredon M, Vermeersch G (1998) Kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy. J Chem Soc Perkin Trans 2(1998):1153–1158CrossRefGoogle Scholar
  4. 4.
    Song L, Yang Y, Zhang Q, Tian H, Zhu W (2011) Synthesis and photochromism of naphthopyrans bearing naphthalimide chromophore: predominant thermal reversibility in color-fading and fluorescence switch. J Photochem Photobiol A Chem 115:14648–14658Google Scholar
  5. 5.
    Aiken S, Booth K, Gabbutt CD, Heron BM, Rice CR, Charaf-Eddin A, Jacquemin D (2014) The first structural and spectroscopic characterisation of a ring-opened form of a 2H-naphtho[1,2-b]pyran: a novel photomerocyanine. Chem Commun 50:7900–7903CrossRefGoogle Scholar
  6. 6.
    Becker RS, Michl J (1969) Photochromism of synthetic and naturally occurring 2H-chromenes and 2H-pyrans. J Am Chem Soc 88:5931–5933CrossRefGoogle Scholar
  7. 7.
    Van Gemert B (1999) Benzo and naphthopyrans (chromens). In: Crano JC, Guglielmetti RJ (eds) Organic photochromic and thermochromic compounds, vol 1. Plenum, New York, pp 111–140Google Scholar
  8. 8.
    Hepworth JD, Heron BM (2006) Photochromic naphthopyrans. In: Kim S-H (ed) Functional dyes. Elsevier, Oxford, pp 85–135CrossRefGoogle Scholar
  9. 9.
    Nakatsuji S, Narashima K, Iyoda M, Akiyama S (1988) A simple and convenient synthesis of aryl-substituted push-pull butadienes from 1,1-diaryl-2-propyn-1-ols. Bull Chem Soc Jpn 61:2253–2255CrossRefGoogle Scholar
  10. 10.
    Clarke DA, Heron BM, Gabbutt CD, Hepworth JD, Partington SM, Corns SN (1999) pH sensitive photochromic dyes. US Pat WO99/031081Google Scholar
  11. 11.
    Kumar A, Van Gemert B, Knowles DB (1995) Substituted naphthopyrans. US Pat 5(458):814Google Scholar
  12. 12.
    Clarke DA, Heron BM, Gabbutt CD, Hepworth JD, Partington SM, Corns SN (2002) Photochromic substituted 2H-naphtho[1,2-b]pyrans. US Pat WO00/35902Google Scholar
  13. 13.
    Van Gemert B (1996) Novel photochromic indeno-fused naphthopyrans. US Pat WO96/14596Google Scholar
  14. 14.
    Momoda J, Izumi S, Yokoyama Y (2015) Substituent effects on the photochromic properties of 3,3-diphenyspiro[benzofluorenopyran-cyclopentaphenanthrene]s. Dyes Pigm 119:95–107CrossRefGoogle Scholar
  15. 15.
    Lin J-S (2003) Interaction between dispersed photochromic compound and polymer matrix. Eur Polymer J 39:1693–1700CrossRefGoogle Scholar

Copyright information

© Springer Japan KK 2017

Authors and Affiliations

  1. 1.TS DepartmentTokuyama Corp. LtdTsukuba-shiJapan
  2. 2.Department of Advanced Materials Chemistry, Graduate School of EngineeringYokohama National University, TokiwadaiHodogayaJapan

Personalised recommendations