Skip to main content
SpringerLink
Log in

The Spectroscopic Behavior of Two New 5-(5-R-6-Hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium Merocyanines in Various Solvents

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Solvatochromic studies on two new merocyanines, prepared from 5-(5-bromo-6-hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate and 5-(5-nitro-6-hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate, were performed in 21 solvents using UV–vis spectroscopy. The VBHB model (J.A. Soroka and K.B. Soroka in J. Phys. Org. Chem. 4:592–604, 1991) was applied to describe their solvatochromic properties.

The results indicate that both dyes exhibit variable solvatochromism, i.e. it is positive in nonpolar solvents and negative in polar aprotic and protic solvents. The solvatochromic shifts of both merocyanines are approximately 8000 cm−1(for toluene to water). The studies revealed that these two merocyanines exist in solutions as nonpolar (quinoid, i.e. vinylogous amide, V) or polar (zwitterionic, i.e. betaine, B) forms in their ground state, respectively. The dye with a nitro substituent can also form a hydrogen-bonded betaine (HB). This dye is found to be the first compound in the whole group of 7H-indolo[1,2-a]quinolinium merocyanines that does not comply with the VBHB model assumptions.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Scheme 3
Fig. 4

Similar content being viewed by others

References

  1. Reichardt, Ch.: Solvents and Solvent Effects in Organic Chemistry, 3th edn. VCH, Weinheim (2003)

    Google Scholar 

  2. Soroka, J.A., Soroka, K.B.: Solvatochromism of dyes. Part I. Solvatochromism of merocyanines. Derivatives of the 7H-indolo[1,2-a]quinolinium system. A new model of solvatochromism. J. Phys. Org. Chem. 4, 592–604 (1991)

    Article  CAS  Google Scholar 

  3. Wróblewska, E.K., Soroka, J.A., Soroka, K.B., Gąsiorowska, M.: Solvatochromism of dyes. Part IV—Energetic characteristic of merocyanine derivatives of 1-phenyl-2-[2-(3-X-4-hydroxy-5-R-phenyl)ethenyl]-3,3-dimethyl-3H-indolium cation. J. Phys. Org. Chem. 18, 347–352 (2005)

    Article  Google Scholar 

  4. Dimroth, K., Reichardt, Ch., Siepmann, T., Bohlmann, F.: Über Pyridinium-N-phenol-betaine und ihre Verwendung zur Charakterisierung der Polarität von Lösungsmitteln. Liebigs Ann. Chem. 661, 1–37 (1963)

    Article  CAS  Google Scholar 

  5. Dimroth, K., Reichardt, Ch.: Über Pyridinium-N−phenol-betaine und ihre Verwendung zur Charakterisierung der Polarität von Lösungsmitteln. V. Erweiterung der Lösungsmittelpolaritätsskala durch Verwendung Alkyl-substituierter Pyridinium-N-phenol-betaine. Justus Liebigs Ann. Chem. 727, 93–105 (1969)

    Article  CAS  Google Scholar 

  6. Sawicka, M.J., Soroka, J.A., Wróblewska, E.K., Zawadzka, I.K.: Synthesis and UV–vis study of a new strongly solvatochromic merocyanine-like dye with modified donor part. Pol. J. Chem. 80, 1337–1351 (2006)

    CAS  Google Scholar 

  7. Sawicka, M.J., Soroka, J.A., Gąsiorowska, M.: A new method for the preparation of solvatochromic 5-(5-X-6-hydroxynaphthyl-2)-7H-indolo[1,2-a]quinolinium merocyanines Pol. J. Chem. Technol. 12(1), 17–22 (2010)

    Article  Google Scholar 

  8. Chandra, A.K., Uchimaru, T.: The O–H bond dissociation energies of substituted phenols and proton affinities of substituted phenoxide ions: a DFT study. Int. J. Mol. Sci. 3, 407–422 (2002)

    Article  CAS  Google Scholar 

  9. Pimentel, G., McClellan, A.: The Hydrogen Bond. Freeman, San Francisco (1960)

    Google Scholar 

  10. Jiang, L., Lai, L.: CH⋯O hydrogen bonds at protein–protein interfaces. J. Biol. Chem. 277(40), 37732–37740 (2002)

    Article  CAS  Google Scholar 

  11. Domagała, M., Grabowski, S.J.: Hydrocarbons as proton donors in C–H⋯N and C–H⋯S hydrogen bonds. Chem. Phys. 367, 1–6 (2010)

    Article  Google Scholar 

  12. Zierkiewicz, W.: Modelling of interactions between volatile anesthetics (halothane, enflurane) and aromatic compounds, ab initio study. Chem. Phys. 373, 243–250 (2010)

    Article  CAS  Google Scholar 

  13. Wojtulewski, S., Grabowski, S.J.: Different donors and acceptors for intramolecular hydrogen bonds. Chem. Phys. Lett. 378, 388–394 (2003)

    Article  CAS  Google Scholar 

  14. Gore, M.G.: Spectrophotometry & Spectrofluorimetry. Practical Approach. Oxford University Press Inc., New York (2000)

    Google Scholar 

  15. Wróblewska, E.K., Soroka, J.A., Soroka, K.B., Gąsiorowska, M., Sawicka, M.J.: Calibration surfaces in analysis of ternary mixtures. Part 2. Degree of analytical utility of solvatochromic indicator. Chem. Anal. (Warsaw) 49, 729–738 (2004)

    Google Scholar 

  16. Lang, L.: Absorption spectra in the ultraviolet and visible region. XIV, No 2480, Académiai Kiadó, Budapest (1970)

Download references

Author information

Authors and Affiliations

  1. Department of Instrumental Analysis, Institute of Chemistry and Environmental Protection, West Pomeranian University of Technology, Piastów Ave. 42, 71-065, Szczecin, Poland

    Marta J. Sawicka, Jacek A. Soroka, Monika Gąsiorowska & Elwira K. Wróblewska

Authors
  1. Marta J. Sawicka
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jacek A. Soroka
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Monika Gąsiorowska
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Elwira K. Wróblewska
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marta J. Sawicka.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sawicka, M.J., Soroka, J.A., Gąsiorowska, M. et al. The Spectroscopic Behavior of Two New 5-(5-R-6-Hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium Merocyanines in Various Solvents. J Solution Chem 41, 25–35 (2012). https://doi.org/10.1007/s10953-011-9778-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-011-9778-z

Keywords

Search

Navigation