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A new method for the preparation of solvatochromic 5-(5-X-6-hydroxynaphthyl-2)-7H-indolo[1,2-a]quinolinium merocyanines

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Języki publikacji
EN
Abstrakty
EN
A new method for the preparation of 7H-indolo[1,2-a]quinolinium solvatochromic dye precursors has been investigated. 5-(6-Hydroxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorate, 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 obtained via demethylation of the corresponding 5-(5-X-6-methoxynaphthyl-2)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium salts. The application of pyridinium hydrochloride in the demethylation of the methoxy perchlorates allowed to obtain the products with the almost quantitative yield in a very short time, especially when the reaction was carried out using microwave irradiation.
Rocznik
Strony
17--22
Opis fizyczny
Bibliogr. 18 poz., rys., tab.
Twórcy
autor
autor
  • Institute of Chemistry and Environmental Protection, Section of Instrumental Analysis, West Pomeranian University of Technology, Szczecin, ul. Piastów 42, 71-065 Szczecin, msawicka@zut.edu.p
Bibliografia
  • 1. Reichardt, Ch. (2003). Solvents and Solvent Effects in Organic Chemistry (3th ed). VCH, Weinheim.
  • 2. Nigam, S., Stephens, M., de Juan, A. & Rutan, S.C. (2001). Characterization of the Polarity of Reversed-Phase Liquid Chromatographic Stationary Phases in the Presence of 1-Propanol Using Solvatochromism and Multivariate Curve Resolution. Anal. Chem. 73(2), 290 – 297. DOI: 10.1021/ ac000836k.
  • 3. Wróblewska, E.K., Soroka, J.A. & Rosłaniec, Z. (2005). Solvatochromic dyes in the investigations of polymers' structures. Part II. Diffusion profiles in selected copoly(esterethers). Polimery. 50(4), 286 – 290 (in Polish).
  • 4. Moyano, F., Silber, J.J. & Correa, N.M. (2008). On the investigation of the bilayer functionalities of 1,2-di-oleoyl-sn-glycero-3-phosphatidylcholine (DOPC) large unilamellar vesicles using cationic hemicyanines as optical probes: a wavelength-selective fluorescence approach. J. Colloid Interface Sci. 317(1), 332 – 345. DOI: 10.1016/j.jcis.2007.09.051.
  • 5. Tsai, C.C., Lin, H.M. & Lee, M.J. (2007). Solubility of Disperse Yellow 54 in Supercritical Carbon Dioxide with or without Cosolvent. Fluid Phase Equilibr. 260(2), 287 – 294. DOI: 10.1016/j.fluid.2007.07.070.
  • 6. Thirumoorthi, A. & Elango, K.P. (2007). Electrochemical oxidation of substituted benzylamines in aquo-acetic acid medium: substituent and solvent effects. J. Chem. Sci. 119(4), 289 – 294.
  • 7. Labuszewska, K., Cegielski, R., Niedbalska, M. & Martynski, T. (2008). Stilbazolium merocyanine systems in Langmuir and Langmuir-Blodgett molecular layers. Colloid Surfaces A. 321(1-3), 39 – 42. DOI: 10.1016/j.colsurfa. 2008.02.039.
  • 8. Zawadzka, I.K., Soroka, J.A., Gąsiorowska, M. & Sawicka, M.J. (2007). Novel solvatochromic 1,3,2-dioxaborines as composition indicators in analysis of organic solvent mixtures. Chem. Anal. (Warsaw). 53, 83 – 108 .
  • 9. Soroka, J.A. & Soroka, K.B. (1991). 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(10), 592 – 604. DOI: 10.1002/poc.610041003.
  • 10. Soroka, K.B. & Soroka, J.A. (1989). Photochemistry of hemicyanines. Part III. Synthesis of 5-(hydroxyaryl)-7,7-dimethyl-7H-indolo[1,2-a]quinolinium perchlorates and determination of their acidities. Chem. Scripta 29, 167 – 171.
  • 11. Sawicka, M.J., Soroka, J.A., Wróblewska, E.K. & Zawadzka, I.K. (2006). Synthesis and UV-vis study of a new strongly solvatochromic merocyanine-like dye with modified donor part. Polish J. Chem. 80, 1337 – 1351.
  • 12. Wróblewska, E.K., Soroka, J.A. & Soroka, K.B. (2002). Solvatochromism and solvatochromic dyes. Wiad. Chem. 56(1-2), 113 – 150 (in Polish).
  • 13. Weissman, S.A. & Zewge, D. (2005) Recent advances in ether dealkylation. Tetrahedron 61(33), 7833 – 7863. DOI: 10.1016/j.tet.2005.05.041.
  • 14. Kulkarni, P.P., Kadam, A.J., Mane, R.B., Desai, U.V. & Wadgaonkar, P.P.(1999). Demethylation of methyl aryl ethers using pyridine hydrochloride in solvent-free conditions under microwave irradiation. J. Chem. Research (S), 394 – 395. DOI: 10.1039/a901278h.
  • 15. Sawicka, M.J., Soroka, J.A., Soroka, K.B. & Gąsiorowska, M. (2007). Microwaves in organic synthesis. Wiad. Chem. 61(11-12), 891 – 911 (in Polish).
  • 16. Medson Electronics, Co Ltd., Poznań – Paczkowo.
  • 17. Perreux, L. & Loupy, A. (2001). A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron, 57(45), 9199 – 9223. DOI: 10.1016/S0040-4020(01)00905-X.
  • 18. Lidström, P., Tierney, J., Wathey, B. & Westman, J. (2001). Microwave assisted organic synthesis -a review. Tetrahedron 57(45), 9225 – 9283. DOI: 10.1016/S0040-4020(01)00906-1.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BPS2-0054-0040
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