Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access April 25, 2010

Fluorescent chemosensors for metal ions based on 3-(2-benzoxazol-5-yl)alanine skeleton

  • Magda Milewska EMAIL logo , Katarzyna Guzow and Wiesław Wiczk
From the journal Open Chemistry

Abstract

The ability of new chelate ligands, benzoxazol-5-yl-alanine derivatives substituted in position 2 by heteroaromatic substituent, to form complexes with selected metal ions in acetonitrile are studied by means of absorption and steady-state and time-resolved fluorescence spectroscopy. Among the ligands studied, only azaaromatic derivatives form stable complexes with transition metal ions in the ground state. Their absorption bands are bathochromically shifted enabling to use those ligands as ratiometric sensors. The fluorescence of each ligand is quenched by metal ions, however, in the presence of Cd(II) and Zn(II) ions a new red shifted emission band is observed.

[1] A.P. de Silva et al., Chem. Rev. 97, 1515 (1997) http://dx.doi.org/10.1021/cr960386p10.1021/cr960386pSearch in Google Scholar

[2] B. Valuer, I. Leray, Coord. Chem. Rev. 205, 3 (2000) http://dx.doi.org/10.1016/S0010-8545(00)00246-010.1016/S0010-8545(00)00246-0Search in Google Scholar

[3] J.F. Callan, A.P. de Silva, D.C. Magri, Tetrahedron 61, 8551 (2005) http://dx.doi.org/10.1016/j.tet.2005.05.04310.1016/j.tet.2005.05.043Search in Google Scholar

[4] K. Rurack, Spectrochim. Acta A 57, 2161 (2001) http://dx.doi.org/10.1016/S1386-1425(01)00492-910.1016/S1386-1425(01)00492-9Search in Google Scholar

[5] C. Bargossi, M.C. Fiorini, M. Montalti, L. Prodi, N. Zaccheroni, Coord. Chem. Rev. 208, 17 (2000) http://dx.doi.org/10.1016/S0010-8545(00)00252-610.1016/S0010-8545(00)00252-6Search in Google Scholar

[6] E.A. Medlycott, G.S. Hanan, Coord. Chem. Rev. 250, 1763 (2006) http://dx.doi.org/10.1016/j.ccr.2006.02.01510.1016/j.ccr.2006.02.015Search in Google Scholar

[7] F.N. Castellano, I.E. Pomestchenko, E. Shikhova, F. Hua, M.L. Muro, N. Rajapakse, Coord. Chem. Rev. 250, 1819 (2006) http://dx.doi.org/10.1016/j.ccr.2006.03.00710.1016/j.ccr.2006.03.007Search in Google Scholar

[8] G. Xue et al., Tetrahedron 58, 4809 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00451-910.1016/S0040-4020(02)00451-9Search in Google Scholar

[9] M.C. Kimber, I.B. Mahadevan, S.F. Lincoln, A.D. Ward, E.R.T. Tiekink, J. Org. Chem. 65, 8204 (2000) http://dx.doi.org/10.1021/jo000678x10.1021/jo000678xSearch in Google Scholar PubMed

[10] C.J. Fahrni, T.V. O`Halloran, J. Am. Chem. Soc. 121, 11448 (1999) http://dx.doi.org/10.1021/ja992709f10.1021/ja992709fSearch in Google Scholar

[11] G. Xue et al., Tetrahedron 57, 7623 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00746-310.1016/S0040-4020(01)00746-3Search in Google Scholar

[12] J.M. Castagnetto, J.W. Canary, Chem. Commun. 203 (1998) 10.1039/a705443bSearch in Google Scholar

[13] Y. Mikata, M. Wakamatsu, S. Yano, Dalton Tran. 545 (2005) 10.1039/b411924jSearch in Google Scholar PubMed

[14] D.-Y. Wu et al., Dalton Trans 29, 3528 (2006) http://dx.doi.org/10.1039/b605653a10.1039/b605653aSearch in Google Scholar PubMed

[15] M.D. Shults, D.A. Pearce, B. Imperiali, J. Am. Chem. Soc. 125, 10591 (2003) http://dx.doi.org/10.1021/ja035598010.1021/ja0355980Search in Google Scholar PubMed

[16] K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, T. Nagano, J. Am. Chem. Soc. 126, 12470 (2004) http://dx.doi.org/10.1021/ja046933310.1021/ja0469333Search in Google Scholar PubMed

[17] L. Xue, H.-H. Wang, X.-J. Wang, H. Jiang, Inorg. Chem. 47, 4310 (2008) http://dx.doi.org/10.1021/ic702393z10.1021/ic702393zSearch in Google Scholar PubMed

[18] Z. Xu, X. Qian, J. Cui, R. Zhang, Tetrahedron 62, 10117 (2006) http://dx.doi.org/10.1016/j.tet.2006.08.05010.1016/j.tet.2006.08.050Search in Google Scholar

[19] K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, T. Nagano, Angew. Chem. Int. Ed. 42, 2996 (2003) http://dx.doi.org/10.1002/anie.20035112210.1002/anie.200351122Search in Google Scholar PubMed

[20] V. Balzani, G. Bergamini, F. Marchioni, P. Ceroni, Coord. Chem. Rev. 250, 1254 (2006) http://dx.doi.org/10.1016/j.ccr.2005.11.01310.1016/j.ccr.2005.11.013Search in Google Scholar

[21] V. Amendola et al., Coord. Chem. Rev. 250, 273 (2006) http://dx.doi.org/10.1016/j.ccr.2005.04.02210.1016/j.ccr.2005.04.022Search in Google Scholar

[22] K. Tanaka, H. Kumagai, H. Aoki, M. Deguchi, S. Iwata, J. Org. Chem. 66, 7328 (2001) http://dx.doi.org/10.1021/jo010462a10.1021/jo010462aSearch in Google Scholar

[23] J.-S. Youk, Y.H. Kim, E.-J. Kim, N.J. Youn, S.-K. Chang, Bull. Korean Chem. Soc. 25, 869 (2004) http://dx.doi.org/10.5012/bkcs.2004.25.6.86910.5012/bkcs.2004.25.6.869Search in Google Scholar

[24] M.G.B. Drew et al., New J. Chem. 28, 462 (2004) http://dx.doi.org/10.1039/b314321j10.1039/b314321jSearch in Google Scholar

[25] K. Guzow et al., J. Photochem. Photobiol. A: Chem. 187, 87 (2007) http://dx.doi.org/10.1016/j.jphotochem.2006.09.01910.1016/j.jphotochem.2006.09.019Search in Google Scholar

[26] K. Guzow, M. Szabelski, J. Malicka, J. Karolczak, W. Wiczk, Tetrahedron 58, 2201 (2002) http://dx.doi.org/10.1016/S0040-4020(02)00092-310.1016/S0040-4020(02)00092-3Search in Google Scholar

[27] SPECFIT/32 Global Analysis System for Windows, Spectrum Software Associates, Bio-Logic Science Instruments Search in Google Scholar

[28] K. Rurack, R. Radeglia, Eur. J. Inorg. Chem. 2271 (2000) 10.1002/1099-0682(200010)2000:10<2271::AID-EJIC2271>3.0.CO;2-3Search in Google Scholar

[29] M.M. Henary, Y. Wu, C.J. Fahrni, Chem. Eur. J. 10, 3015 (2004) http://dx.doi.org/10.1002/chem.20030529910.1002/chem.200305299Search in Google Scholar

[30] K. Guzow, M. Milewska, D. Wróblewski, A. Giełdoń, W. Wiczk, Tetrahedron 60, 11889 (2004) http://dx.doi.org/10.1016/j.tet.2004.09.08410.1016/j.tet.2004.09.084Search in Google Scholar

[31] M. Milewska, A. Skwierawska, K. Guzow, D. Szmigiel, W. Wiczk, Inorg. Chem. Commun. 8, 947 (2005) http://dx.doi.org/10.1016/j.inoche.2005.07.00810.1016/j.inoche.2005.07.008Search in Google Scholar

[32] B. Valeur, In: J.R. Lakowicz (Ed.), Principles of Fluorescent Probe Design for Ion Recognition. In Topics in Fluorescence Spectroscopy, Probe Design and Chemical Sensing (Plenum Press, New York, 1994) vol. 4, 21–48 10.1007/0-306-47060-8_2Search in Google Scholar

[33] R. Snyder, A.C. Testa, J. Phys. Chem. 88, 5948 (1984) http://dx.doi.org/10.1021/j150668a04010.1021/j150668a040Search in Google Scholar

[34] H. Irving, R.J.P. Williams, Nature (London) 162, 746 (1948) http://dx.doi.org/10.1038/162746a010.1038/162746a0Search in Google Scholar

[35] M.M. Henary, C.J. Fahrni, J. Phys. Chem. A 106, 5210 (2002) http://dx.doi.org/10.1021/jp014634j10.1021/jp014634jSearch in Google Scholar

[36] M. Taki, J.L. Wolford, T.V. O’Halloran, J. Am. Chem. Soc. 126, 712 (2004) http://dx.doi.org/10.1021/ja039073j10.1021/ja039073jSearch in Google Scholar PubMed

[37] C.J. Chang, J. Jaworski, E.M. Nolan, M. Sheng, S.J. Lippard, Proc. Natl. Acad. Sci. USA 101, 1129 (2004) http://dx.doi.org/10.1073/pnas.030807910010.1073/pnas.0308079100Search in Google Scholar PubMed PubMed Central

Published Online: 2010-4-25
Published in Print: 2010-6-1

© 2010 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Downloaded on 28.3.2024 from https://www.degruyter.com/document/doi/10.2478/s11532-010-0036-9/html
Scroll to top button