Factors Affecting the Efficiency of Excited-States Interactions of Complexes between Some Visible Light-Emitting Lanthanide Ions and Cyclophanes Containing Spirobiindanol Phosphonates

Attia, M. S.; Khalil, M. M. H.; Abdel-Shafi, Ayman A.; Attia, G. M.; Failla, Salvatore; Consiglio, Giuseppe; Finocchiaro, Paolo; Abdel-Mottaleb, M. S. A.

doi:https://doi.org/10.1155/2007/12530

International Journal of Photoenergy

On this page

Abstract References Copyright Related Articles

Research Article | Open Access

Volume 2007 | Article ID 012530 | https://doi.org/10.1155/2007/12530

Factors Affecting the Efficiency of Excited-States Interactions of Complexes between Some Visible Light-Emitting Lanthanide Ions and Cyclophanes Containing Spirobiindanol Phosphonates

M. S. Attia,^1,2M. M. H. Khalil,^1,2Ayman A. Abdel-Shafi,^1,2G. M. Attia,¹Salvatore Failla,³Giuseppe Consiglio,³Paolo Finocchiaro,³and M. S. A. Abdel-Mottaleb^1,2

Academic Editor: Stefan Lis

Received03 May 2006

Revised06 Sept 2006

Accepted07 Sept 2006

Published13 Dec 2006

Abstract

The efficiency of excited-states interactions between lanthanide ions Tb3+ and Eu3+ and some new cyclophanes (I, II, and III) has been studied in different media. High luminescence quantum yield values for terbium and europium complexes in DMSO and PMMA were obtained. The photophysical properties of the green and red emissive Tb3+ and Eu3+ complexes have been elucidated, respectively.

References

L. Charbonnière, R. Ziessel, M. Guardigli, A. Roda, N. Sabbatini, and M. Cesario, “Lanthanide tags for time-resolved luminescence microscopy displaying improved stability and optical properties,” Journal of the American Chemical Society, vol. 123, no. 10, pp. 2436–2437, 2001.
View at: Publisher Site | Google Scholar
A. Mayer and S. Neuenhofer, “Luminescent labels—more than just an alternative to radioisotopes?” Angewandte Chemie, vol. 33, no. 10, pp. 1044–1072, 1994.
View at: Publisher Site | Google Scholar
V. W.-W. Yam and K. K.-W. Lo, “Recent advances in utilization of transition metal complexes and lanthanides as diagnostic tools,” Coordination Chemistry Reviews, vol. 184, no. 1, pp. 157–240, 1999.
View at: Publisher Site | Google Scholar
J. Meyer and U. Karst, “Enzyme-linked immunosorbent assays based on peroxidase labels and enzyme-amplified lanthanide luminescence detection,” Analyst, vol. 126, no. 2, pp. 175–178, 2001.
View at: Publisher Site | Google Scholar
K. J. Valenzano, W. Miller, J. N. Kravitz, P. Samama, D. Fitzpatrick, and K. Seeley, “Development of a fluorescent ligand-binding assay using the AcroWell filter plate,” Journal of Biomolecular Screening, vol. 5, no. 6, pp. 455–461, 2000.
View at: Publisher Site | Google Scholar
C. Petrovas, S. M. Daskas, and E. S. Lianidou, “Determination of tumor necrosis factor- $α$ (TNF- $α$ ) in serum by a highly sensitive enzyme amplified lanthanide luminescence immunoassay,” Clinical Biochemistry, vol. 32, no. 4, pp. 241–247, 1999.
View at: Publisher Site | Google Scholar
N. Sabbatini, M. Guardigli, and J.-M. Lehn, “Luminescent lanthanide complexes as photochemical supramolecular devices,” Coordination Chemistry Reviews, vol. 123, no. 1-2, pp. 201–228, 1993.
View at: Publisher Site | Google Scholar
S. W. Magennis, S. Parsons, A. Corval, J. D. Woollins, and Z. Pikramenou, “Imidodiphosphinate ligands as antenna units in luminescent lanthanide complexes,” Chemical Communications, no. 1, pp. 61–62, 1999.
View at: Publisher Site | Google Scholar
C. Fischer, G. Sarti, A. Casnati et al., “ $2, 2^{'}$ -bipyridine lariat calixcrowns: a new class of encapsulating ligands forming highly luminescent ${Eu}^{3 +}$ and ${Tb}^{3 +}$ complexes,” Chemistry - A European Journal, vol. 6, no. 6, pp. 1026–1034, 2000.
View at: Publisher Site | Google Scholar
Y. Bretonnière, R. Wietzke, C. Lebrun, M. Mazzanti, and J. Pécaut, “Solid-state and solution structure of lanthanide complexes of a new nonadentate tripodal ligand containing phenanthroline binding units,” Inorganic Chemistry, vol. 39, no. 16, pp. 3499–3505, 2000.
View at: Publisher Site | Google Scholar
G. R. Motson, O. Mamula, J. C. Jeffery, J. A. McCleverty, M. D. Ward, and A. Von Zelewsky, “A $C_{3}$ -symmetric chiral hexadentate podand ligand based on a tris(pyrazolyl)borate core,” Journal of the Chemical Society, Dalton Transactions, no. 9, pp. 1389–1391, 2001.
View at: Publisher Site | Google Scholar
J.-C. G. Bünzli and C. Piguet, “Lanthanide-containing molecular and supramolecular polymetallic functional assemblies,” Chemical Reviews, vol. 102, no. 6, pp. 1897–1928, 2002.
View at: Publisher Site | Google Scholar
D. Parker, R. S. Dickins, H. Puschmann, C. Crossland, and J. A. K. Howard, “Being excited by lanthanide coordination complexes: aqua species, chirality, excited-state chemistry, and exchange dynamics,” Chemical Reviews, vol. 102, no. 6, pp. 1977–2010, 2002.
View at: Publisher Site | Google Scholar
J. Kido and Y. Okamoto, “Organo lanthanide metal complexes for electroluminescent materials,” Chemical Reviews, vol. 102, no. 6, pp. 2357–2368, 2002.
View at: Publisher Site | Google Scholar
X.-S. Tai and M.-Y. Tan, “Studies on synthesis, infrared and fluorescence spectra of new europium (III) and terbium (III) complexes with an $β$ -diketonate-type ligand,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 61, no. 8, pp. 1767–1770, 2005.
View at: Publisher Site | Google Scholar
P. Lenaerts, K. Driesen, R. Van Deun, and K. Binnemans, “Covalent coupling of luminescent tris(2-thenoyltrifluoroacetonato) lanthanide(III) complexes on a merrifield resin,” Chemistry of Materials, vol. 17, no. 8, pp. 2148–2154, 2005.
View at: Publisher Site | Google Scholar
P. Lenaerts, E. Ryckebosch, K. Driesen et al., “Study of the luminescence of tris(2-thenoyltrifluoroacetonato) lanthanide(III) complexes covalently linked to 1,10-phenanthroline- functionalized hybrid sol-gel glasses,” Journal of Luminescence, vol. 114, no. 1, pp. 77–84, 2005.
View at: Publisher Site | Google Scholar
Y.-L. Zhang, W.-W. Qin, W.-S. Liu, M.-Y. Tan, and N. Tang, “Studies on synthesis and infrared and fluorescence spectra of new europium and terbium complexes with an amide-based open-chain crown ether,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 58, no. 10, pp. 2153–2157, 2002.
View at: Publisher Site | Google Scholar
W. Qin, Y. Zhang, W. Liu, and M. Tan, “Synthesis and infrared and fluorescence spectral properties of luminescent terbium and europium complexes with open-chain carboxylate crown ethers,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 59, no. 13, pp. 3085–3092, 2003.
View at: Publisher Site | Google Scholar
S. W. Magennis, J. Craig, A. Gardner et al., “Crown ether lanthanide complexes as building blocks for luminescent ternary complexes,” Polyhedron, vol. 22, no. 5, pp. 745–754, 2003.
View at: Publisher Site | Google Scholar
M.-T. Alonso, E. Brunet, O. Juanes, and J.-C. Rodríguez-Ubis, “Synthesis and photochemical properties of new coumarin-derived ionophores and their alkaline-earth and lanthanide complexes,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 147, no. 2, pp. 113–125, 2002.
View at: Publisher Site | Google Scholar
V. Bekiari, P. Judeinstein, and P. Lianos, “A sensitive fluorescent sensor of lanthanide ions,” Journal of Luminescence, vol. 104, no. 1-2, pp. 13–15, 2003.
View at: Publisher Site | Google Scholar
L. Hao, W. Wei, W. Yaanhua, and L. Zhenzhong, “Fluorescence study of Eu chelates in solution and polymer matrix,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 61, no. 11-12, pp. 2687–2690, 2005.
View at: Publisher Site | Google Scholar
F. R. Gonçalves e Silva, O. L. Malta, C. Reinhard et al., “Visible and near-infrared luminescence of lanthanide-containing dimetallic triple-stranded helicates: energy transfer mechanisms in the ${Sm}^{III}$ and ${Yb}^{III}$ molecular edifices,” Journal of Physical Chemistry A, vol. 106, no. 9, pp. 1670–1677, 2002.
View at: Publisher Site | Google Scholar
G. F. de Sá, O. L. Malta, C. de Mello Donegá et al., “Spectroscopic properties and design of highly luminescent lanthanide coordination complexes,” Coordination Chemistry Reviews, vol. 196, no. 1, pp. 165–195, 2000.
View at: Google Scholar
M. P. Lowe and D. Parker, “pH switched sensitisation of europium(III) by a dansyl group,” Inorganica Chimica Acta, vol. 317, no. 1-2, pp. 163–173, 2001.
View at: Publisher Site | Google Scholar
F. Vögtle, M. Gorka, V. Vicinelli, P. Ceroni, M. Maestri, and V. Balzani, “A dendritic antenna for near-infrared emission of ${Nd}^{3 +}$ ions,” ChemPhysChem, vol. 2, no. 12, pp. 769–773, 2001.
View at: Publisher Site | Google Scholar
G. Consiglio, S. Failla, P. Finocchiaro, and F. Marchetti, “Synthesis and clathration properties of novel chiral cyclophanes containing spirobiindanol phosphonates unit,” Journal of Supramolecular Chemistry, vol. 2, no. 1–3, pp. 293–300, 2003.
View at: Publisher Site | Google Scholar
G. Consiglio, P. Finocchiaro, S. Failla et al., “Stereochemistry of congested cyclophanes containing chiral spirobiindanol phosphonates: syntheses, X-ray structure, HPLC enantioresolution and clathration properties,” European Journal of Organic Chemistry, vol. 1999, no. 11, pp. 2799–2806, 1999.
View at: Publisher Site | Google Scholar
J. N. Millar, Standards in Fluorescence Spectrometry, Chapman & Hall, New York, NY, USA, 1981.
H. A. Benesi and J. H. Hildebrand, “A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons,” Journal of the American Chemical Society, vol. 71, no. 8, pp. 2703–2707, 1949.
View at: Publisher Site | Google Scholar
S. M. de B. Costa, M. M. Queimado, and J. J. R. Fraústo da Silva, “Energy transfer in complexes between a crown ether and various lanthanide salts,” Journal of Photochemistry, vol. 2, no. 1, pp. 31–39, 1980.
View at: Publisher Site | Google Scholar
S. Umetani, S. Tsurubou, T. Sasaki, and Y. Komatsu, “Macrocyclic ligand as ion size selective masking reagent in metal ion separation,” RIKEN Review, no. 35, pp. 110–114, 2001, Focused on New Trends in Bio-Trace Elements Research.
View at: Google Scholar
S. Bhattacharyya, M. B. Roy, and S. Ghosh, “The dependence of photoinduced energy transfer on the orientation of the acceptor with respect to the $π$ -plane of the donor in naphthalene-linked crown ether- ${Tb}^{3 +}$ complexes,” Chemical Physics, vol. 300, no. 1–3, pp. 295–304, 2004.
View at: Publisher Site | Google Scholar
S. Bhattacharyya, L. R. Sousa, and S. Ghosh, “Dual phosphorescence from 2,3-naphtho-17-crown-5 ether in ethanol glass at 77 K,” Chemical Physics Letters, vol. 269, no. 3-4, pp. 314–320, 1997.
View at: Publisher Site | Google Scholar
J. D. Simon, W. R. Moomaw, and T. M. Ceckler, “The structure and NMR and electronic spectra of europium(III) crown ether complexes in solution,” Journal of Physical Chemistry, vol. 89, no. 26, pp. 5659–5665, 1985.
View at: Publisher Site | Google Scholar
Y.-L. Zhang, W.-W. Qin, W.-S. Liu, M.-Y. Tan, and N. Tang, “Studies on synthesis and infrared and fluorescence spectra of new europium and terbium complexes with an amide-based open-chain crown ether,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 58, no. 10, pp. 2153–2157, 2002.
View at: Publisher Site | Google Scholar
D. F. Parra, H. F. Brito, J. D. R. Matos, and L. C. Dias, “Enhancement of the luminescent intensity of the novel system containing ${Eu}^{3 +}$ - $β$ -diketonate complex doped in the epoxy resin,” Journal of Applied Polymer Science, vol. 83, no. 12, pp. 2716–2726, 2002.
View at: Publisher Site | Google Scholar
O. S. Wolfbeis and M. Leiner, “Mapping of the total fluorescence of human blood serum as a new method for its characterization,” Analytica Chimica Acta, vol. 167, pp. 203–215, 1985.
View at: Publisher Site | Google Scholar
G. D. Christian, J. B. Callis, and E. R. Davidson, Modern Luminescence Spectroscopy, edited by E. L. Wehry, vol. 4, Plenum Press, New York, NY, USA, 1981, chapter 4.
L. R. Sousa and J. M. Larson, “Crown ether model systems for the study of photoexcited state response to geometrically oriented perturbers. The effect of alkali metal ions on emission from naphthalene derivatives,” Journal of the American Chemical Society, vol. 99, no. 1, pp. 307–310, 1977.
View at: Publisher Site | Google Scholar
S. Ghosh, M. Petrin, A. H. Maki, and L. R. Sousa, “Effect of metal ion perturbers on the triplet state of naphthalene in naphthalene crown ether-metal ion complexes. II. Stark ,” Journal of Chemical Physics, vol. 88, no. 5, pp. 2913–2918, 1988.
View at: Publisher Site | Google Scholar
S. I. Klink, L. Grave, D. N. Reinhoudt et al., “A systematic study of the photophysical processes in polydentate triphenylene-functionalized ${Eu}^{3 +}$ , ${Tb}^{3 +}$ , ${Nd}^{3 +}$ , ${Yb}^{3 +}$ , and ${Er}^{3 +}$ complexes,” Journal of Physical Chemistry A, vol. 104, no. 23, pp. 5457–5468, 2000.
View at: Publisher Site | Google Scholar
E. Bakier and M. S. A. Abdel-Mottaleb, “Factors affecting light energy transfer in some samarium complexes,” International Journal of Photoenergy, vol. 7, no. 1, pp. 51–58, 2005.
View at: Publisher Site | Google Scholar
I. M. Warner, J. B. Callis, E. R. Davidson, and G. D. Christian, “Multicomponent analysis in clinical chemistry by use of rapid scanning fluorescence spectroscopy,” Clinical Chemistry, vol. 22, no. 9, pp. 1483–1492, 1976.
View at: Google Scholar
R. O. Nodari, S. M. Tsail, R. L. Gilbertson, and P. Gepts, “Towards an integrated linkage map of common bean 2. Development of an RFLP-based linkage map,” Theoretical and Applied Genetics, vol. 85, no. 5, pp. 513–520, 1993.
View at: Publisher Site | Google Scholar
K. Schumann, A. Baumann, and W. Nagl, “Localization of phaseolin genes in the polytene chromosomes of Phaseolus coccineus (Leguminosae),” Genetica, vol. 83, no. 1, pp. 73–76, 1990.
View at: Publisher Site | Google Scholar
J. Jiang, B. S. Gill, G.-L. Wang, P. C. Ronald, and D. C. Ward, “Metaphase and interphase fluorescence in situ hybridization mapping of the rice genome with bacterial artificial chromosomes,” Proceedings of the National Academy of Sciences of the United States of America, vol. 92, no. 10, pp. 4487–4491, 1995.
View at: Publisher Site | Google Scholar

Copyright

Copyright © 2007 M. S. Attia et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

PDF Download Citation Order printed copies

Views

308

Downloads

1006

Citations