Skip to main content
Log in

Electron-deficient molecules: photophysical, electrochemical, and thermal investigations of naphtho[2,3-f]quinoxaline-7,12-dione derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In this work, we have prepared a series of 2,3-disubstituted naphtho[2,3-f]quinoxaline-7,12-dione derivatives by condensing 1,2-diaminoanthraquinone and various benzil compounds in glacial acetic acid with excellent yield and fully characterized. Optical properties of the synthesized compounds were studied in solvents of varying polarity and thin solid film. Electrochemical properties of the compounds were studied by the cyclic voltammetry. The ionization potentials (HOMO) and electron affinity (LUMO) were found to be in the range of −6.364 to −6.644 eV and −3.247 to −3.511 eV, respectively. Thermal investigations were carried out by thermogravimetric analysis and differential scanning calorimetry.

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

Access this article

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

Instant access to the full article PDF.

Figure 1
Figure 2
Figure 3
Figure 4

Similar content being viewed by others

References

  1. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Robinson, R. G.; Barnett, S. F.; Defeo-Jones, D.; Jones, R. E.; Hartman, G. D.; Huff, J. R.; Huber, H. E.; Duggan, M. E. Bioorg. Med. Chem. Lett. 2005, 15, 761.

    Article  CAS  Google Scholar 

  2. Loriga, M.; Piras, S.; Sanna, P.; Paglietti, G. Farmaco 1997, 52, 157.

    CAS  Google Scholar 

  3. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Bioorg. Med. Chem. Lett. 2004, 14, 541.

    Article  CAS  Google Scholar 

  4. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem . 2002, 45, 5604.

    Article  CAS  Google Scholar 

  5. He, W.; Myers, M. R.; Hanney, B.; Spada, A. P.; Bilder, G.; Galzinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, M. H. Bioorg. Med. Chem. Lett. 2003, 13, 3097.

    Article  CAS  Google Scholar 

  6. Katoh, A.; Yoshida, T.; Ohkanda, J. Heterocycles 2000, 52, 911.

    Article  CAS  Google Scholar 

  7. Thomas, K. R. J.; Velusamy, M.; Lin, J. T.; Chuen, C. H.; Tao, Y. T. Chem. Mater. 2005, 17, 1860.

    Article  CAS  Google Scholar 

  8. Shaikh, A. M.; Sharma, B. K.; Kamble, R. M. J. Chem. Sci. 2015, 127, 1571.

    Article  CAS  Google Scholar 

  9. Shaikh, A. M.; Sharma, B. K.; Kamble, R. M. Can. Chem. Trans. 2015, 3, 158.

    Google Scholar 

  10. Shirota, Y. J. J. Mat. Chem. 2000, 10, 1.

    Article  CAS  Google Scholar 

  11. Baghbanian, S. M. Chin. Chem. Lett. 2015, 26, 1113.

    Article  CAS  Google Scholar 

  12. Srinivas, Ch.; Kumar, Ch. N. S. S. P.; Rao, V. J.; Palaniappan. S. Catal. Lett. 2008, 121, 291.

  13. Srinivas, Ch.; Kumar, Ch. N. S. S. P.; Rao, V. J.; Palaniappan. S. J. Mol. Catal. A: Chem. 2007, 265, 227.

  14. Ulla, H.; Garudachari, B.; Satyanarayan, M. N.; Umesh, G.; Isloor, A. M. Opt. Mater. (Amsterdam, Neth.) 2014, 36, 704.

  15. Agarwal, N.; Nayak, P. K.; Ali, F.; Patankar, M. P.; Narasimhan, K. L.; Periasamy, N. Synth. Met. 2011, 161, 466.

    Article  CAS  Google Scholar 

  16. Sharma, B. K.; Shaikh, A. M.; Agarwal, N.; Kamble, R. M. RSC Adv. 2016, 6, 17129.

    Article  CAS  Google Scholar 

  17. Kamble, R. M.; Shaikh, A. M.; Sharma, B. K. Chem. Sci. Trans. 2015, 4, 781.

    CAS  Google Scholar 

  18. Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556.

    Article  CAS  Google Scholar 

  19. Fukuda, T.; Kanbara, T.; Yamamoto, T.; Ishikawa, K.; Takezoe, H.; Fukuda, A. Appl. Phys. Lett. 1996, 68, 2346.

    Article  CAS  Google Scholar 

  20. O'Brien, D.; Weaver, M. S.; Lidzey, D. G.; Bradley, D. D. C. Appl. Phys. Lett. 1996, 69, 881.

    Article  Google Scholar 

  21. Cui, Y.; Zhang, X.; Jenekhe, S. Macromolecules 1999, 32, 3824.

    Article  CAS  Google Scholar 

  22. Sharma, B. K.; Shaikh, A. M.; Kamble, R. M. J. Chem. Sci. 2015, 127, 2063.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Rajesh M. Kamble.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(2), 110–115

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 2675 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shaikh, A.M., Sharma, B.K. & Kamble, R.M. Electron-deficient molecules: photophysical, electrochemical, and thermal investigations of naphtho[2,3-f]quinoxaline-7,12-dione derivatives. Chem Heterocycl Comp 52, 110–115 (2016). https://doi.org/10.1007/s10593-016-1842-6

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1842-6

Keywords

Navigation