Skip to main content
SpringerLink
Log in

Synthesis and photochromism of novel spiro(indoline-2,3′-naphtho[2,1-b][1,4]oxazine)

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A series of novel spirooxazine(SPO) derivatives containing nitrogen heterocycles was synthesized and characterized by 1H NMR spectra, Fourier transform infrared(FTIR) spectra, mass spectra(MS) and elemental analysis, and their photochromic behaviors were fully investigated in solvents and polymer media. In solvents, they displayed excellent photochromism properties such as high photochromic response and fast thermal bleaching rate. Especially, compounds 1 and 4 exhibited strong fluorescence intensities in dichloromethane solution. It was additionally found that compound 4 showed high fatigue resistence in poly(methyl methacrylate)(PMMA) film, and the thermal decay curves were fitted with biexponential function in PMMA film.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Berkovic G., Krongauz V., Weiss V., Chem. Rev., 2000, 100, 1741

    Article  CAS  Google Scholar 

  2. Chatterjee M. N., Kay E. R., Leigh D. A., J. Am. Chem. Soc., 2006, 128, 4058

    Article  CAS  Google Scholar 

  3. Tian H., Chen B. Z., Tu H. Y., Mullen K., Adv. Mater., 2002, 14, 918

    Article  CAS  Google Scholar 

  4. Jiang H. B., Gong C. B., Wang Q., Tang Q., Ma X. B., Chem. J. Chinese Universities, 2014, 35(9), 2043

    CAS  Google Scholar 

  5. Sun Y., Wang X. S., Lu Y. M., Xuan L. M., Xia S., Feng W., Han X. K., Chem. Res. Chinese Universities, 2014, 30(5), 703

    Article  CAS  Google Scholar 

  6. Wang S., Yu C. Y., Choi M. S., Kim S. H., Dyes Pigment, 2008, 77, 245

    Article  CAS  Google Scholar 

  7. Parthenopoulos D. A., Rentzepis P. M., Science, 1989, 245, 843

    Article  CAS  Google Scholar 

  8. Lu Z., Feng Y. L., Chen Z. B., Xiao J. P., Yan W. P., Fan M. G., Chem. J. Chinese Universities, 2005, 26(8), 1451

    CAS  Google Scholar 

  9. Kong L. C., Wong H. L., Tam A. Y. Y., Lam V. H., Wu L. X., Yam V. W. W., ACS Appl. Mater. Interfaces, 2014, 6, 155

    Article  Google Scholar 

  10. Tan T. F., Chen P. L., Huang H. M., Meng J. B., Tetrahedron, 2005, 61, 8192

    Article  CAS  Google Scholar 

  11. Tang X. C., Jia D. Z., Zhang X. G., Xia X., Zhou Z. Y., Chem. Res. Chinese Universities, 2000, 16(2), 116

    CAS  Google Scholar 

  12. Chu N. Y. C., Can. J. Chem., 1983, 61, 300

    Article  CAS  Google Scholar 

  13. Schneider S., Mindl A., Elfmger G., Melzig M., Phys. Chem. Neue. Folge., 1987, 91, 1222

    CAS  Google Scholar 

  14. Fan M. G., Ming Y. F., Liang Y. C., Zhang X. Y., Jin S., Yao S., Lin N. Y., J. Chem. Soc. Perkin Trans. 2, 1994, 1397

    Google Scholar 

  15. Bohne C., Fan M. G., Li Z. J., Liang Y. C., Lusztyk J., Scaiano J. C., J. Photochem. Photobiol. A, Chem., 1992, 66, 79

    Article  CAS  Google Scholar 

  16. Watkins D. L., Fujiwara T. S., J. Photochem. Photobiol. A, 2012, 228, 51

    Article  CAS  Google Scholar 

  17. Sami S., Hooshang V., Abdolhossien M., Omid L., Molecules, 2010, 15, 2491

    Article  Google Scholar 

  18. Wang J., Cao W., Sua J., Tian H., Huang Y., Sun Z., Dyes Pigment, 2003, 57, 171

    Article  CAS  Google Scholar 

  19. Baeyer A., Villiger V., Ber. Dtsch. Chem. Ges., 1902, 35, 1189

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Nankai University, Tianjin, 300071, P. R. China

    Hong Li, Meili Pang, Xinfu Guo & Jiben Meng

Authors
  1. Hong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Meili Pang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xinfu Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jiben Meng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Meili Pang.

Additional information

Supported by the National Natural Science Foundation of China(Nos.20971071, 20602020).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, H., Pang, M., Guo, X. et al. Synthesis and photochromism of novel spiro(indoline-2,3′-naphtho[2,1-b][1,4]oxazine). Chem. Res. Chin. Univ. 31, 357–361 (2015). https://doi.org/10.1007/s40242-015-4482-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-015-4482-y

Keywords

Search

Navigation