Skip to main content
SpringerLink
Log in

Solvent and Substituents Effect on the UV/Vis Absorption Spectra of Novel Acidochromic 2-Aminothiazole Based Disperse Mono Azo Dyes

  • Published:
Fibers and Polymers Aims and scope Submit manuscript

Abstract

The effect of solvent atmosphere on the electronic absorption properties of 2-aminothiazole based monoazo disperse dyes are studied. The synthesized monoazo dyes with different substituents on the para position of phenyl ring led to changes in the absorption properties of these dyes. Further, the positive solvatochromism data was evaluated to get the excited and ground state dipole moment ratio of the dyes. The Kamlet-Taft and Catalan polarity scales were employed wherein the solvent basicity and dipolarity is responsible for the bathochromic shift with increase in solvent polarity. The free amino group in the dyes made it responsive towards protonation by trifluoroacetic acid. The acidochromic behavior of the dyes was studied and D1, D3, and D4 exhibited major color change to longer wavelength with emergence of a new red shifted absorption band at 556 nm, 580 nm, and 540 nm, respectively, in their absorption spectra. Thus with help of simple UV-Vis absorption studies, we have studied the intermolecular interactions of the 2-aminothiazole based mono azo acidochromic probe.

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. B. Chen, R. Zhao, B. Wang, R. Droghini, J. Lajeunesse, P. Sirard, M. Endo, B. Balasubramanian, and J. C. Barrisha, Arkivoc, 2010, 32 (2010).

    Article  Google Scholar 

  2. R. Mocelo-Castell, C. Villanueva-Novelo, D. Cáceres-Castillo, R. M. Carballo, R. F. Quijano-Quiñones, M. Quesadas-Rojas, Z. Cantillo-Ciau, R. Cedillo-Rivera, R. E. Moo-Puc, L. M. Moujir, and G. J. Mena-Rejón, Open Chem., 13, 1127 (2015).

    Article  CAS  Google Scholar 

  3. H. E. Gaffer, M. M. Fouda, and M. E. Khalifa, Molecules, 21, 122 (2016).

    Article  CAS  PubMed Central  Google Scholar 

  4. S. Annadurai, R. Martinez, D. J. Canney, T. Eidem, P. M. Dunman, and M. Abou-gharbia, Bioorg. Med. Chem. Lett., 22, 7719 (2012).

    Article  CAS  PubMed  Google Scholar 

  5. M. Özkütük, E. Ipek, B. Aydiner, S. Mamas, and Z. Seferoglu, J. Mol. Struct., 1108, 521 (2016).

    Article  CAS  Google Scholar 

  6. A. D. Towns, Dyes Pigm., 42, 3 (1999).

    Article  CAS  Google Scholar 

  7. H. R. Maradiya and V. S. Patel, Fiber. Polym., 2, 153 (2001).

    Article  CAS  Google Scholar 

  8. H. R. Maradiya, J. Saudi Chem. Soc., 16, 69 (2012).

    Article  CAS  Google Scholar 

  9. G. G. Malik, P. C. Patel, J. H. Tailor, and S. K. Zadafiya, Int. Res. J. Nat. Appl. Sci., 6, 108 (2014).

    Google Scholar 

  10. K. Singh, S. Singh, and J. A. Taylor, Dyes Pigm., 54, 189 (2002).

    Article  CAS  Google Scholar 

  11. H. R. Maradiya, J. Saudi Chem. Soc., 14, 77 (2010).

    Article  CAS  Google Scholar 

  12. G. Egilmez, G. A. Süer, and O. Özgüner, World's largest Science, Technology & Medicine Open Access Book Publisher: Des. Control Appl. Mechatron. Syst. Eng., 135–152 (2012).

    Google Scholar 

  13. R. Kammel, D. Tarabová, O. Machalický, M. Nepraš, B. Frumarová, and J. Hanusek, Dyes Pigm., 128, 101 (2016).

    Article  CAS  Google Scholar 

  14. R. M. El-Shishtawy, F. Borbone, Z. M. Al-Amshany, A. Tuzi, A. Barsella, A. M. Asiri, and A. Roviello, Dyes Pigm., 96, 45 (2013).

    Article  CAS  Google Scholar 

  15. H. Osman, A. Arshad, C. K. Lam, and M. C. Bagley, Chem. Cent. J., 6, 156 (2012).

    Google Scholar 

  16. J. Safari, Z. Abedi-Jazini, Z. Zarnegar, and M. Sadeghi, Catal. Commun., 77, 108 (2016).

    Article  CAS  Google Scholar 

  17. T. V. Sravanthi and S. L. Manju, J. Fluoresc., 25, 1727 (2015).

    Article  CAS  PubMed  Google Scholar 

  18. P. Suppan and C. Tsiamis, Spectrochim. Acta Part A: Mol. Spectrosc., 36, 971 (1980).

    Article  Google Scholar 

  19. N. H. Ayachit, J. Electron Spectros. Relat. Phenomena, 180, 14 (2010).

    Article  CAS  Google Scholar 

  20. N. H. Ayachit, D. K. Deshpande, M. A. Shashidhar, and K. S. Rao, Spectrochim. Acta Part A: Mol. Spectrosc., 42, 585 (1986).

    Article  Google Scholar 

  21. N. H. Ayachit, Chem. Phys. Lett., 164, 253 (1989).

    Article  CAS  Google Scholar 

  22. M. J. Kamlet, J. L. Abboud, and R. W. Taft, J. Am. Chem. Soc., 99, 6027 (1977).

    Article  CAS  Google Scholar 

  23. M. J. Kamlet and R. W. Taft, J. Am. Chem. Soc., 98, 377 (1976).

    Article  CAS  Google Scholar 

  24. M. J. Kamlet, J. Abboud, M. H. Abraham, and R. W. Taft, J. Org. Chem., 48, 2877 (1983).

    Article  CAS  Google Scholar 

  25. C. Azarias, S. Budzák, A. D. Laurent, G. Ulrich, and D. Jacquemin, Chem. Sci., 4, 1166 (2016).

    Google Scholar 

  26. M. S. Zakerhamidi, A. Ghanadzadeh, and M. Moghadam, Chem. Sci. Trans., 1, 1 (2012).

    Article  CAS  Google Scholar 

  27. J. Catalán, J. Palomar, C. Díaz, J. L. G. de Paz, J. Phys. Chem. A., 101, 5183 (1997).

    Article  Google Scholar 

  28. J. Catalán and C. Díaz, J. Org. Chem., 885 (1999).

    Google Scholar 

  29. J. Catalán, J. Phys. Chem. B., 113, 5951 (2009).

    Article  CAS  PubMed  Google Scholar 

  30. M. S. Zakerhamidi, M. Keshavarz, H. Tajalli, A. Ghanadzadeh, S. Ahmadi, M. Moghadam, S. H. Hosseini, and V. Hooshangi, J. Mol. Liq., 154, 94 (2010).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Dyestuff Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai, 400 019, India

    Manali Rajeshirke, Mayuri Kadam & Nagaiyan Sekar

Authors
  1. Manali Rajeshirke
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mayuri Kadam
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nagaiyan Sekar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nagaiyan Sekar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rajeshirke, M., Kadam, M. & Sekar, N. Solvent and Substituents Effect on the UV/Vis Absorption Spectra of Novel Acidochromic 2-Aminothiazole Based Disperse Mono Azo Dyes. Fibers Polym 20, 320–327 (2019). https://doi.org/10.1007/s12221-019-8317-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12221-019-8317-1

Keywords

Search

Navigation