Abstract
Polycondensation reactions of phenols with phthalic anhydride were carried out in the presence of ferric hydrogensulphate under melt conditions. The reactions proceeded in short reaction times by using a catalytic amount of Fe(HSO4)3 and the corresponding fluorescein derivatives were obtained in high yields. The simplicity, scale-up, along with the use of an inexpensive, non-toxic, recyclable catalyst of an environmentally benign nature, are other remarkable features of the procedure. The absorption and emission properties of these fluorescein derivatives were studied.
[1] Cihelník, S., Stibor, I., & Lhoták, P. (2002). Solvent-free synthesis of sulfonephthaleins, sulfonefluoresceins and fluoresceins under microwave irradiation. Collection of Czechoslovak Chemical Communications, 67, 1779–1789. DOI: 10.1135/cccc20021779. http://dx.doi.org/10.1135/cccc2002177910.1135/cccc20021779Search in Google Scholar
[2] Eshghi, H. (2006). Ferric hydrogensulfate catalysed Schmidt reaction of ketones to amides under solvent-free conditions. Journal of the Chinese Chemical Society, 53, 987–990. 10.1002/jccs.200600131Search in Google Scholar
[3] Eshghi, H., Bakavoli, M., & Moradi, H. (2009a). Ferric hydrogensulfate catalyzed aerobic oxidative coupling of 2-naphthols in water or under solvent free conditions. Chinese Chemical Letters, 20, 663–667. DOI: 10.1016/j.cclet.2008.12. 045. http://dx.doi.org/10.1016/j.cclet.2008.12.045Search in Google Scholar
[4] Eshghi, H., Bakavoli, M., & Moradi, H. (2008a). Fe(HSO4)3: An efficient, heterogeneous and reusable catalyst for the synthesis of 14-aryl- or alkyl-14H-dibenzo[a,j]xanthenes. Chinese Chemical Letters, 19, 1423–1426. DOI: 10.1016/j.cclet.2008. 09.048. http://dx.doi.org/10.1016/j.cclet.2008.09.04810.1016/j.cclet.2008.09.048Search in Google Scholar
[5] Eshghi, H., Bakavoli, M., Moradi, H., & Davoodnia, A. (2009b). Fe(HSO4)3 and Fe(HSO4)3/DMSO as efficient, heterogeneous, and reusable catalyst systems for the oxidative coupling of thiols. Phosphorus, Sulfur and Silicon and the Related Elements, 184, 3110–3118. DOI: 10.1080/10426500802704654. http://dx.doi.org/10.1080/1042650080270465410.1080/10426500802704654Search in Google Scholar
[6] Eshghi, H., Mirzaie, N., & Asoodeh, A. (2011). Synthesis of fluorescein aromatic esters in the presence of P2O5/SiO2 as catalyst and their hydrolysis studies in the presence of lipase. Dyes and Pigments, 89, 120–126. DOI: 10.1016/j.dyepig.2010. 09.013. http://dx.doi.org/10.1016/j.dyepig.2010.09.01310.1016/j.dyepig.2010.09.013Search in Google Scholar
[7] Eshghi, H., Rahimizadeh, M., & Saberi, S. (2008b). Fe(HSO4)3 as an inexpensive, eco-friendly, heterogeneous and reusable catalyst for acetal/ketal formation and their facile regeneration. Catalysis Communications, 9, 2460–2466. DOI: 10.1016/j.catcom.2008.06.015. http://dx.doi.org/10.1016/j.catcom.2008.06.01510.1016/j.catcom.2008.06.015Search in Google Scholar
[8] Fatima, K., Nosheen, S., Azhar, H., & Azhar, M. (2009). Synthesis and application of eosin. Pakistan Journal of Agricultural Sciences, 46, 1–7. Search in Google Scholar
[9] Gronowska, J., & Dabkowska-Naskret, H. (1981). Fluoran derivatives. Part IX. Synthesis of halofluorans. Polish Journal of Chemistry, 55, 2151–2163. Search in Google Scholar
[10] Heller, E., Klöckner, J., Lautenschläger, W., & Holzgrabe, U. (2010). Online monitoring of microwave-enhanced reactions by UV/Vis spectroscopy. European Journal of Organic Chemistry, 2010, 3569–3573. DOI: 10.1002/ejoc.201000441. http://dx.doi.org/10.1002/ejoc.20100044110.1002/ejoc.201000441Search in Google Scholar
[11] Hilderbrand, S. A., & Weissleder, R. (2007). One-pot synthesis of new symmetric and asymmetric xanthene dyes. Tetrahedron Letters, 48, 4383–4385. DOI: 10.1016/j.tetlet.2007.04. 088. http://dx.doi.org/10.1016/j.tetlet.2007.04.08810.1016/j.tetlet.2007.04.088Search in Google Scholar PubMed PubMed Central
[12] Kojima, H., Nakatsubo, N., Kikuchi, K., Kawahara, S., Kirino, Y., Nagoshi, H., Hirata, Y., & Nagano, T. (1998). Detection and imaging of nitric oxide with novel fluorescent indicators: diaminofluoresceins. Analytical Chemistry, 70, 244–2453. DOI: 10.1021/ac9801723. http://dx.doi.org/10.1021/ac980172310.1021/ac9801723Search in Google Scholar PubMed
[13] Miura, T., Urano, Y., Tanaka, K., Nagano, T., Ohkubo, K., & Fukuzumi, S. (2003). Rational design principle for modulating fluorescence properties of fluorescein-based probes by photoinduced electron transfer. Journal of the American Chemical Society, 125, 8666–8671. DOI: 10.1021/ja035282s. http://dx.doi.org/10.1021/ja035282s10.1021/ja035282sSearch in Google Scholar PubMed
[14] Mizukami, S., Kikuchi, K., Higuchi, T., Urano, Y., Mashima, T., Tsuruo, T., & Nagano, T. (1999). Imaging of caspase-3 activation in HeLa cells stimulated with etoposide using a novel fluorescent probe. FEBS Letters, 453, 356–360. DOI: 10.1016/S0014-5793(99)00755-3. http://dx.doi.org/10.1016/S0014-5793(99)00755-310.1016/S0014-5793(99)00755-3Search in Google Scholar
[15] Mugherli, L., Burchak, O. N., Chatelain, F., & Balakirev, M. Y. (2006). Fluorogenic ester substrates to assess proteolytic activity. Bioorganic & Medicinal Chemistry Letters, 16, 4488–4491. DOI: 10.1016/j.bmcl.2006.06.037. http://dx.doi.org/10.1016/j.bmcl.2006.06.03710.1016/j.bmcl.2006.06.037Search in Google Scholar PubMed
[16] Peng, T., & Yang, D. (2010). HKGreen-3: A rhodol-based fluorescent probe for peroxynitrite. Organic Letters, 12, 4932–4935. DOI: 10.1021/ol102182j. http://dx.doi.org/10.1021/ol102182j10.1021/ol102182jSearch in Google Scholar PubMed
[17] Rahimizadeh, M., Eshghi, H., Bakhtiarpoor, Z., & Pordel, M. (2009). Ferric hydrogensulfate as a recyclable catalyst for the synthesis of some new bis(indolyl)methane derivatives. Journal of Chemical Research, 2009, 269–270. DOI: 10.3184/030823409X430194. http://dx.doi.org/10.3184/030823409X43019410.3184/030823409X430194Search in Google Scholar
[18] Sun, W.-C., Gee, K. R., Klaubert, D. H., & Haugland, R. P. (1997). Synthesis of fluorinated fluoresceins. The Journal of Organic Chemistry, 62, 6469–6475. DOI: 10.1021/jo9706178. http://dx.doi.org/10.1021/jo970617810.1021/jo9706178Search in Google Scholar
[19] Tanaka, K., Miura, T., Umezawa, N., Urano, Y., Kikuchi, K., Higuchi, T., & Nagano, T. (2001). Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen. Journal of the American Chemical Society, 123, 2530–2536. DOI: 10.1021/ja0035708. http://dx.doi.org/10.1021/ja003570810.1021/ja0035708Search in Google Scholar PubMed
[20] Tsien, R. Y., & Waggoner, A. (1995). Fluorophores for confocal microscopy. In J. B. Pawley (Ed.), Handbook of biological confocal microscopy (2nd ed., pp. 267–279). New York, NY, USA: Plenum Press. Search in Google Scholar
[21] Weissleder, R., & Ntziachristos, V. (2003). Shedding light onto live molecular targets. Nature Medicine, 9, 123–128. DOI: 10.1038/nm0103-123. http://dx.doi.org/10.1038/nm0103-12310.1038/nm0103-123Search in Google Scholar PubMed
[22] Windholz, M. (1976). The Merck index (9th ed.). Rahway, NJ, USA: Merck. Search in Google Scholar
[23] Woodroofe, C. C., Lim, M. H., Bu. W., & Lippard, S. J. (2005). Synthesis of isomerically pure carboxylate- and sulfonatesubstituted xanthene fluorophores. Tetrahedron Letters, 61, 3097–3105. DOI: 10.1016/j.tet.2005.01.024. 10.1016/j.tet.2005.01.024Search in Google Scholar
[24] Zaikova, T. O., Rukavishnikov, A. V., Birrell, G. B., Griffith, O. H., & Keana, J. F. W. (2001). Synthesis of fluorogenic substrates for continuous assay of phosphatidylinositol-specific phospholipase C. Bioconjugate Chemistry, 12, 307–313. DOI: 10.1021/bc0001138. http://dx.doi.org/10.1021/bc000113810.1021/bc0001138Search in Google Scholar PubMed
© 2011 Institute of Chemistry, Slovak Academy of Sciences
