Skip to main content

Diarylethenes with Heterocyclic Aryl Groups

  • Chapter
Organic Photochromic and Thermochromic Compounds

Part of the book series: Topics in Applied Chemistry ((TAPP))

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. Saltiel and J. L. Charlton, in: Rearrangement in Ground and Excited States (P. de Mayo, ed.), Vol. 3, p. 25, Academic Press, New York (1980).

    Google Scholar 

  2. M. Irie and M. Mohri, Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives, J. Org. Chem. 53, 803–805 (1988).

    Article  CAS  Google Scholar 

  3. K. Uchida, S. Nakamura, and M. Irie, Photochromism of diarylethene derivatives. Stability of the closed-ring forms, Res. Chem. Intermed. 21, 861–876 (1995).

    CAS  Google Scholar 

  4. M. Hanazawa, R. Sumiya, Y. Horikawa, and M. Irie, Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(2-methylbenzo[b]thiophen-3-yl)perfluorocycloalkene derivatives, J. Chem. Soc. Chem. Commun., 1992, 206–207.

    Google Scholar 

  5. M. Irie, K. Sakemura, M. Okinaka, and K. Uchida, Photochromism of dithienylethenes with electron-donating substituents, J. Org. Chem. 60, 8305–8309 (1995).

    Article  CAS  Google Scholar 

  6. S._L. Gilat, S. H. Kawai, and J.-M. Lehn, Light-triggered molecular devices: photochemical switching of optical and electrochemical properties in molecular wire-type diarylethene species, Chem. Eur. J 1, 275–284 (1995).

    CAS  Google Scholar 

  7. S._H. Kawai, S. L. Gilat, R. Ponsient, and J.-M. Lehn, A Dual-mode molecular switching device: bis-phenolic diarylethenes with integrated photochromic and electrochromic properties, Chem. Eur. J. 1, 285–293 (1995).

    CAS  Google Scholar 

  8. K. Uchida, T. Ishikawa, M. Takeshita, and M. Irie, Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(thiazolyl)perfluorocyclopentenes, Tetrahedron, 54, 6627–6638 (1998).

    CAS  Google Scholar 

  9. S. Nakamura and M. Irie, Thermally irreversible photochromic systems. A theoretical study, J. Org. Chem. 53, 6136–6138 (1988).

    CAS  Google Scholar 

  10. K. Uchida, Y. Nakayama, and M. Irie, Thermally irreversible photochromic systems. Reversible photocyclization of 1,2 bis-(benzo[b]thiophen-3-yl)ethene derivatives, Bull. Chem. Soc. Jpn. 63, 1311–1315 (1990).

    CAS  Google Scholar 

  11. Y. Nakayama, K. Hayashi, and M. Irie, Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-diselenenylethene and 1,2-diindolylethene derivatives, J. Org. Chem. 55, 2592–2596 (1990).

    CAS  Google Scholar 

  12. K. Uchida, S. Nakamura, and M. Irie, Thermally irreversible photochromic systems. Substituent effect on the absorption wavelength of 11,12-dicyano-5a,5b-dihydro-5a,5b-dimethylbenzo [1,2-b:6,5-b′]bis[1]benzothiophene, Bull. Chem. Soc. Jpn. 65, 430–435 (1992).

    CAS  Google Scholar 

  13. Y. Nakayama, K. Hayashi, and M. Irie, Thermally irreversible photochromic systems. Reversible photocyclization of nonsymmetric diarylethene derivatives, Bull. Chem. Soc. Jpn. 64, 789–795 (1991).

    CAS  Google Scholar 

  14. M. Irie, Advances in photochromic materials for optical data storage media, Jpn. J Appl. Phys. 28, Suppl. 3, 215–219 (1989).

    CAS  Google Scholar 

  15. M. Irie, Photochromic diarylethenes for optical data storage media, Mol. Cryst. Liq. 227, 263–270 (1993).

    CAS  Google Scholar 

  16. S._L. Gilat, S. H. Kawai, and J.-M. Lehn, Light-triggered electrical and optical switching devices, J. Chem. Soc. Commun. 1993, 1439–1442.

    Google Scholar 

  17. G._M. Tsivgolulis, and J.-M. Lehn, Photonic molecular devices: reversibly photoswitchable fluorophores for nondestructive readout for optical memory, J Chem. Soc. Chem. Commun. 1995, 1119–1122.

    Google Scholar 

  18. K. Uchida and M. Irie, A photochromic dithienylethene that turns yellow by UV irradiation, Chem. Lett. 1995, 969–970.

    Google Scholar 

  19. H. Miyasaka, S. Arai, A. Tabata, T. Nobuto, N. Mataga, and M. Irie, Picosecond laser photolysis studies on photochromic reactions of 1,2-bis-(2,4,5-trimethyl-3-thienyl)maleic anhydride in solutions, Chem. Phys. Lett. 230, 249–254 (1994).

    CAS  Google Scholar 

  20. N. Tamai, T. Saika, T. Shimidzu, and M. Irie, Femtosecond Dynamics of a thiophene oligomer with a photoswitch by transient absorption spectroscopy, J. Phys. Chem. 100, 4689–4692 (1996).

    Article  CAS  Google Scholar 

  21. M. Irie, O. Miyatake, and K. Uchida, Blocked photochromism of diarylethenes, J. Am. Chem. Soc. 114, 8715–8716 (1992).

    Article  CAS  Google Scholar 

  22. M. Irie, O. Miyatake, K. Uchida, and T. Eriguchi, Photochromic diarylethenes with intralocking arms, J. Am. Chem. Soc. 116, 9894–9900 (1994).

    Article  CAS  Google Scholar 

  23. T. Koshido, T. Kawai, and K. Yoshino, Optical and electrochemical properties of cis-1,2-dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene, J. Phys. Chem. 99, 6110–6114 (1995).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2002 Kluwer Academic Publishers

About this chapter

Cite this chapter

Irie, M. (2002). Diarylethenes with Heterocyclic Aryl Groups. In: Crano, J.C., Guglielmetti, R.J. (eds) Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry. Springer, Boston, MA. https://doi.org/10.1007/0-306-46911-1_6

Download citation

  • DOI: https://doi.org/10.1007/0-306-46911-1_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-45882-8

  • Online ISBN: 978-0-306-46911-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics