Skip to main content
SpringerLink
Log in

Quinoline-Containing π-Conjugated Systems: Synthesis, Research, and Application of Quinophthalone Dyes

  • REVIEW ARTICLE
  • Published:
Reviews and Advances in Chemistry Aims and scope Submit manuscript

Abstract

Here we present the literary review concerning methods of synthesis and application fields of substituted quinophthalones, an interesting class of heterocyclic compounds containing fragments of substituted/unsubstituted quinolines and phthalic anhydride in their structure. Such compounds have an extended π-conjugated system and are, therefore, most often used as dyes.

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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Scheme 1.
Fig. 5.
Fig. 6.
Fig. 7.
Scheme 2.
Scheme 3.
Scheme 4.
Scheme 5.
Scheme 6.
Scheme 7.
Fig. 8.
Scheme 8.
Scheme 9.
Scheme 10.
Fig. 9.
Scheme 11.
Fig. 10.
Scheme 12.
Fig. 11.
Fig. 12.
Fig. 13.
Scheme 13.
Scheme 14.
Fig. 14.
Scheme 15.
Fig. 15.
Fig. 16.
Fig. 17.
Fig. 18.
Scheme 16.
Scheme 17.
Fig. 19.
Scheme 18.
Fig. 20.
Fig. 21.
Scheme 19.
Fig. 22.
Scheme 20.
Fig. 23.
Fig. 24.
Fig. 25.
Fig. 26.

REFERENCES

  1. Chen, D., Su, S.-J., and Cao, Y., J. Mater. Chem. C, 2014, vol. 2, no. 45, p. 9565.

    Article  ADS  CAS  Google Scholar 

  2. Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsyklov (Theoretical Foundations of Heterocyclic Chemistry), Moscow: Khimiya, 1985.

  3. Bettenhausen, J., Greczmiel, M., Jandke, M., and Strohriegl P., Synth. Met., 1997, vol. 91, nos. 1–2, p. 223.

    Article  CAS  Google Scholar 

  4. Karastatiris, P., Mikroyannidis, J.A., Spiliopoulos, I.K, Kulkarni, A.P., and Jenekhe, S.A., Macromolecules, 2004, vol. 37, no. 21, p. 7867.

    Article  ADS  Google Scholar 

  5. Hwang, F.-M., Chen, H.-Y., Chen, P.-S., Liu, C.-S., Chi, Y., Shu, C.-F., Wu, F.-I., Chou, P.-T., Peng, S.-M., and Lee, G.-H., Inorg. Chem., 2005, vol. 44, no. 5, p. 1344.

    Article  CAS  PubMed  Google Scholar 

  6. Morin, J.-F. and Leclerc, M., Macromolecules, 2002, vol. 35, no. 22, p. 8413.

    Article  ADS  CAS  Google Scholar 

  7. Kulkarni, A.P., Zhu, Y., and Jenekhe, S.A., Macromolecules, 2005, vol. 38, no. 5, p.1553.

    Article  ADS  CAS  Google Scholar 

  8. Nosova, E.V., Achelle, S., Lipunova, G.N., Charushin, V.N., and Chupakhin, O.N., Russ. Chem. Rev., 2019, vol. 88, no. 11, p.1128.

    Article  ADS  CAS  Google Scholar 

  9. Radtke, V.V., in High Performance Pigments, Faulkner, E.B. and Schwartz, R.J., Eds., Weinheim: Wiley, 2009, p. 331.

    Google Scholar 

  10. Manukian, B.K., Niklaus, P., and Ehrsam, H., Helv. Chim. Acta, 1969, vol. 52, no. 5, p. 1259.

    Article  CAS  Google Scholar 

  11. Mitewa, M., Bontchev, P.R., Enchev, V., Minchev, S., and Kashchieva, M., J. Prakt. Chem./Chem.-Ztg., 1985, vol. 327, no. 3, p. 516.

    CAS  Google Scholar 

  12. Kashchieva, M., Stoyanov, Ne., Enchev, V., Minchev, S., Bontchev, P.R., and Mitewa, M., Polyhedron, 1997, vol. 16, no. 10, p. 1693.

    Article  CAS  Google Scholar 

  13. Stoyanova, A., Petkova, G., and Peyerimhoff, S.D., Chem. Phys., 2002, vol. 279, no. 1, p. 1.

    Article  CAS  Google Scholar 

  14. US Patent 6788362, 2004.

  15. US Patent 4785114, 1988.

  16. Kuramoto, N. and Kitao, T., J. Chem. Soc., Chem. Commun., 1979, vol. 8, p. 379.

    Article  Google Scholar 

  17. Chichibabin, A.E. Osnovnye nachala organicheskoi khimii (Fundamentals of Organic Chemistry), vol. 2, Sergeev P.G., Ed., Moscow: Goskhimizdat, 1957, 5th ed.

    Google Scholar 

  18. Neiland, O.Ya. and Katsen, Ya.Ya., Chem. Heterocycl. Compd., 1975, vol. 11, no. 4, p. 381.

    Article  Google Scholar 

  19. Han, G.R., Hwang, D., Lee, S., Lee, J.W., Lim, E., Heo, J., and Kim, S.K., Sci. Rep., 2017, vol. 7, no. 1, p. 3863.

    Article  ADS  PubMed  PubMed Central  Google Scholar 

  20. Dobosz, R., Kolehmainen, E., Valkonen, A., Ośmiałowski, B., and Gawinecki, R., Tetrahedron, 2007, vol. 63, no. 37, p. 9172.

    Article  CAS  Google Scholar 

  21. Haupt, E.T.K., Dieck, H., and Bontchev, P.R., Z. Naturforsch., B, 1987, vol. 42, no. 1, p. 31.

    Article  Google Scholar 

  22. Haupt, E.T.K., Dieck, H, and Bontchev, P.R., Z. Naturforsch., B, 1987, vol.42, no. 11, p. 1419.

    Article  CAS  Google Scholar 

  23. Haupt, E.T.K., Eggers, M., Spectrosc. Lett., 1998, vol. 31, no. 3, p. 521.

    Article  ADS  CAS  Google Scholar 

  24. Bogert, M.T. and Heidelberger, M., J. Am. Chem. Soc., 1912, vol. 34, no. 2, p. 183.

    Article  CAS  Google Scholar 

  25. US Patent 4256901, 1981.

  26. Kogan, I.M., Khimia krasitelei (Dyes Chemistry), Korolyeva, A.I., Ed., Moscow, Goskhimizdat, 1956.

    Google Scholar 

  27. Griffiths, J., in Modern Colorants: Synthesis and Structure, Advances in Color Chemistry Series, Peters, A.T. and Freeman, H.S., Eds., Dordrecht: Springer, 1995, vol. 3, p. 40.

    Google Scholar 

  28. Brooker, L.G.S. and Keyes, G.H., J. Am. Chem. Soc., 1951, vol. 73, no. 11, p. 5356.

    Article  CAS  Google Scholar 

  29. Herbst, W. and Hunger, K., Industrial Organic Pigments: Production, Properties, Applications, New York: Wiley, 1997, 2nd ed.

    Google Scholar 

  30. Jacobsen, E. and Reimer, C.L., Chem. Ber., 1883, vol. 16, p. 2602.

    Article  Google Scholar 

  31. Stepanov, B.I., Vvedenie v knimiyu i tekhnologiyu organicheskikh krasiteltei (Introduction to the Chemistry and Technology of Organic Dyes), Moscow: Khimia, 1984.

  32. US Patent 3872131, 1975.

  33. US Patent 2006022, 1935.

  34. Quinophthalones, Patents for C09B25. https://www.google.com/patents/sitemap/en/Sitemap/C09/C09B/C09B_25.html

  35. US Patent 2211662, 1940.

  36. US Patent 3108109, 1963.

  37. US Patent 5468862, 1995.

  38. Lácová, M. and Chabreček, P., Chem. Pap., 1987, vol. 41, no. 5, p. 709.

    Google Scholar 

  39. Loghmani-Khouzani, H., Sadeghi, M., and Safari, J., Molecules, 2002, vol. 7, no. 2, p. 135.

    Article  CAS  PubMed Central  Google Scholar 

  40. Khalili, S.D., Banitabai koupaie, S.H., and Safari, J., Sci. Iran., 2009, vol. 6, p. 1.

    Google Scholar 

  41. Safari, J., Naeimi, H., Khakpour, A.A., Jondani, R.S., and Khalili, S.D., J. Mol. Catal., A, 2007, vol. 270, nos. 1–2, p. 236.

  42. Sangher, S., Kesornpun, C., Aree, T., Mahidol, C., Ruchirawat, S., and Kittakoop, P, Dyes Pigm., 2020, vol. 178, p. 108341.

  43. Porai-Koshits, A.E. and Chzhevskaya, I.I., Zh. Obsch. Khim., 1956, vol. 26, no. 6, p. 1950.

    CAS  Google Scholar 

  44. Feng, J., Liang, B., Wang, D., Xue, L., and Li, X., Org. Lett., 2008, vol. 10, no. 20. p. 4437.

    Article  CAS  PubMed  Google Scholar 

  45. Miyatake, M. and Ehashi, Sh., Shikizai Kyokaishi, 1971, vol. 4, no. 7, p. 316.

    Google Scholar 

  46. FRG Patent 3329340A1, 1985.

  47. US Patent 5359075, 1994.

  48. US Patent 4500710, 1985.

  49. US Patent 20030172847, 2005.

  50. FRG Patent 1770960, 1975.

  51. FRG Patent 1279258B, 1968.

  52. FRG Patent 2626271, 1976.

  53. Jayesh, M.V., Paul, R., and Shankarling, G.S., Paintindia, 1996, vol. 46, no. 10, p. 45.

    Google Scholar 

  54. Fujii, I., Kodama, T., Yanagihara, N., and Hirayama, N., Anal. Sci., 2004, vol. 20, p. x35.

    Article  CAS  Google Scholar 

  55. JP Patent 51142049, 1976.

  56. JP Patent 51137724, 1976.

  57. Choi, J., Kim, S.H., Lee, W., Chang, J.B., Namgoong, J.W., Kim, Y.H., Han, S.H., and Kim, J.P., Dyes Pigm., 2014, vol.101, p. 186.

    Article  CAS  Google Scholar 

  58. US Patent 20140073794, 2014.

  59. Ozhgikhina, A.V., Shklyaeva, E.V., and Abashev, G.G., Proc. VIII Youth School-Conference on the Modern Aspects of Chemistry, Perm, 2021, p. 161.

  60. Bennett, G.M. and Pratt, W.L.C., J. Chem. Soc., 1929, p. 1465.

  61. Ozhgikhina, A.V., Maiorova, O.A., Zhulanov, V.E., Shklyaeva, E.V., and Abashev, G.G., Proc. VI Youth School-Conference on the Modern Aspects of Chemistry, Perm, 2019, p. 63.

Download references

Funding

This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

Author information

Authors and Affiliations

  1. Perm State National Research University, 614990, Perm, Russia

    E. V. Shklyaeva & G. G. Abashev

  2. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, 614990, Perm, Russia

    G. G. Abashev

  3. AO Medisorb, 614990, Perm, Russia

    A. V. Ozhgikhina

Authors
  1. E. V. Shklyaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Ozhgikhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. G. Abashev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. G. Abashev.

Ethics declarations

CONFLICT OF INTEREST

The authors of this work declare that they have no conflicts of interest.

EDITORIAL STATEMENT

The article underwent additional review by Reviews and Advances in Chemistry and was revised before its publication in Reviews and Advances in Chemistry, as compared to the version published in Russian.

Additional information

Translated by S. Avodkova

Publisher’s Note.

Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shklyaeva, E.V., Ozhgikhina, A.V. & Abashev, G.G. Quinoline-Containing π-Conjugated Systems: Synthesis, Research, and Application of Quinophthalone Dyes. rev. and adv. in chem. 13, 238–264 (2023). https://doi.org/10.1134/S2634827623600196

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2634827623600196

Keywords:

Search

Navigation