A new anthracene derivative of calix[4]arene as a fluorescent chemosensor

A new anthracene derivative of calix[4]arene was synthesized as a highly fluorescent compound. This compound was examined for its fluorescent properties towards different metal ions (Li+, Na+, Mg2+, Ca2+, Ba2+, Ni2+, Cu2+, Zn2+, Pb2+) by UV and fluorescence spectroscopy. On complexation by alkaline earth metal cations and transition metal cations, the fluorescence spectrum was quenched. In particular, Ca2+ caused greater than 98% quenching of the anthracene derivative of calix[4]arene.

A new anthracene derivative of calix[4]arene as a fluorescent chemosensor

A new anthracene derivative of calix[4]arene was synthesized as a highly fluorescent compound. This compound was examined for its fluorescent properties towards different metal ions (Li+, Na+, Mg2+, Ca2+, Ba2+, Ni2+, Cu2+, Zn2+, Pb2+) by UV and fluorescence spectroscopy. On complexation by alkaline earth metal cations and transition metal cations, the fluorescence spectrum was quenched. In particular, Ca2+ caused greater than 98% quenching of the anthracene derivative of calix[4]arene.

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  • Moczar, I.; Peragovics, A.; Baranyai, P.; Toth, K.; Huszthy, P. Tetrahedron 2010, 66, 2953–2960.
  • Desvergne, J.P.; Czarnik, A. W. Eds. Chemosensors of Ion and Molecule Recognition; NATO ASI Series C, Kluwer: Dordrecht, The Netherlands, 1997.
  • Lakowicz, J. R. Principles of Fluorescence Spectroscopy ; 2nd ed., Plenum: New York, 1999.
  • Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59–83.
  • Ni, X. L.; Zeng, X.; Redshaw, C.; Yamato, T. Tetrahedron 2011, 67, 3248–3253.
  • Hung, H. C.; Cheng, C. W.; Wang, Y. Y.; Chen, Y. J.; Chung, W. S. Eur. J. Org. Chem. 2009, 36, 6360–6366.
  • Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes, Inc. Eugene, 19 Kim, Y. H.; Cha, N. R.; Chang, S. K. Tetrahedron Lett. 2002, 43, 3883–3886.
  • Tsubaki, K.; Morimoto, T.; Otsubo, T.; Fuji, K. Org. Lett. 2002, 4, 2301–2304.
  • Lee, K. H.; Lee, H. Y.; Lee, D. H.; Hong, J. I. Tetrahedron Lett. 2001, 42, 5447–5449.
  • Kim, E. J.; Choe, J. I.; Chang, S. Tetrahedron Lett. 2003, 44, 5299–5302.
  • Kumar, M.; Dhir. A.; Bhalla, V. Tetrahedron 2009, 65, 7510–7515.
  • Diamond, D.; McKervey, M. A.; Chem. Soc. Rev. 1996, 25, 15–24.
  • Arnaud-Neu, F.; Barret, G.; Corry, D.; Cremin, S.; Ferguson, G.; Gallagher, J. F.; Harris, S. J.; McKervey, M. A.; Weill, M. J. S. J. Chem. Soc., Perkin Trans. 1997, 2, 575–580. de Namor, A. F. D.; Pugliese, A.; Casal, A. R.; Llerena, M. B.; Aymonino, P. J.; Velarde, F. J. S. Phys. Chem. Chem. Phys. 2000, 2, 4355–4360.
  • Talanova, G. G.; Hwang, H. S., Talanov, V. S.; Bartsch, R. A. Chem. Commun. 1998, 9, 419–420.
  • Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1998, 2, 1307–1312.
  • Budka, J.; Lhotak, P.; Michlova, V.; Stibor, I. Tetrahedron Lett. 2001, 42, 1583–1586.
  • Arena, G.; Contino, A.; Gulino, F. G.; Magri, A.; Sciotto, D.; Ungaro, R. Tetrahedron Lett. 2000, 41, 9327–9330. Rodik, R.; Boiko, V.; Danylyuk, O.; Suwinska, K.; Tsymbal, I.; Slinchenko, N.; Babich, L.; Shlykov, S.; Kosterin, S.; Lipkowskib, J.; Kalchenkoa, V. Tetrahedron Lett. 2005, 46, 7459–7462.
  • Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780–3799.
  • Ocak, U.; Ocak, M.; Surowiec, K.; Bartsch, R. A.; Gorbunova, M. G.; Tu, C.; Surowiec, M. A. J. Incl. Phenom. Macrocycl. Chem. 2009, 63, 131–139.
  • Yun, S.; Ihm, H.; Kim, H. G.; Lee, C. W.; Indrajit, B.; Oh, K. S.; Gong, Y. J.; Lee, J. W.; Yoon, J.; Lee, H. C.; et al. J. Org. Chem. 2003, 68, 2467–2470.
  • Kim, S. K., Yoon, J. Chem. Commun. 2002, 770–771.
  • Liao, J. H.; Chen, C. T.; Fang, J. M. Org. Lett. 2002, 4, 561–564.
  • Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463–9464.
  • Lee, S. H.; Kim, S. K.; Bok, J. H.; Lee, S. H.; Yoon, J.; Lee, K.; Kim, J. S. Tetrahedron Lett. 2005, 46, 8163–8167. Kim, H. J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 7051–7055.
  • Othman, A. B.; Lee, J. W.; Wu, J. S.; Kim, J. S.; Abidi, R.; Thu´ ery, P.; Strub, J. M.; Dorsselaer, A. V.; Vicens, J. J. Org. Chem, 2007, 72, 7633–7640.
  • Sahin, O.; Yilmaz, M. Tetrahedron Lett. 2012, 53, 2319–2324.
  • Gutsche, C. D.; Iqbal, M.; Stewart, D. J. Org. Chem. 1986, 51, 742–745.
  • Collins, M.; McKervey, M. A.; Madigan, E.; Moran, M. B.; Owens, M.; Ferguson, G.; Harris, S. J. J. Chem. Soc. Perkin. Trans., 1991, 1, 3137–3142.
  • Chawla, H. M.; Pant, N.; Srivastava, B.; Upreti, S. Org. Lett. 2006, 8, 2237–2240.
  • Akoz, E.; Erdemir, S.; Yilmaz, M. J. Incl. Phenom. Macrocycl. Chem. 2012, 73, 449–458.
  • Lee, S. H.; Kim, J. Y.; Kim, S. K.; Lee, J. H.; Kim, J. S. Tetrahedron 2004, 60, 5171–5176.
  • Kim, S. H.; Choi, J. K.; Kim, S. K.; Simb, W.; Kim, J. S. Tetrahedron Lett. 2006, 47, 3737–3741.
  • Choi, J. K.; Lee, A.; Kim, S.; Ham, S.; No, K.; Kim, J. S. Org. Lett. 2006, 8, 1601–1604.
  • Bourson, J.; Valeur, B. J. Phys. Chem. 1989, 93, 3871–3876.
  • Ocak, U.; Ocak, M.; Surowiec, K.; Bartsch, R. A.; Gorbunova, M. G.; Tu, C.; Surowiec, M. A. J. Incl. Phenom. Macrocyclic Chem. 2009, 63, 131–139.
  • Valeur, B. Molecular Fluorescence Principles and Applications. Wiley-VCH: Weinheim, Germany, 2001.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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