Photophysical Properties of Rare Earth Diclofenac Complexes in the Solid State

Gina Kaup; Marina M. Lezhnina; Denise Meiners; Peter C. Junk; Ulrich H. Kynast

doi:10.1071/CH15249

RESEARCH ARTICLE

Previous Next Contents Vol 68(11)

Photophysical Properties of Rare Earth Diclofenac Complexes in the Solid State

Gina Kaup ^A , Marina M. Lezhnina ^A , Denise Meiners ^A ^B , Peter C. Junk ^B ^C and Ulrich H. Kynast ^A ^C

+ Author Affiliations

- Author Affiliations

^A Department of Chemical Engineering, Muenster University of Applied Sciences, Stegerwaldsr. 39, 48565 Steinfurt, Germany.

^B College of Science, Technology and Engineering, James Cook University, Townsville, Qld 4811, Australia.

^C Corresponding authors. Email: peter.junk@jcu.edu.au; uk@fh-muenster.de

Australian Journal of Chemistry 68(11) 1735-1740 https://doi.org/10.1071/CH15249
Submitted: 6 May 2015 Accepted: 13 June 2015 Published: 20 July 2015

Abstract

We elaborate on the use of the comparably complex, but widely used and readily accessible pharmaceutical diclofenac, the molecular structure of which contains aromatic units with chloro-, amine-, and carboxylate substituents, all of which were deemed to be useful in the formation of efficiently luminescing rare earth complexes. However, efficient luminophores with quantum yields of 48 % in the case of Tb³⁺ could only be obtained by the additional employment of chelating N-donors (1,10-phenanthroline and 2,2′-bipyridine), while analogous Eu³⁺ complexes remained inefficient with quantum yields below 13 %. They nevertheless exhibited luminescence decay times of up to 1668 µs – unusual for such low efficiencies, which suggest an intermediate involvement of the diclofenac triplet state. Finally, the new complexes were also tested for their applicability as an analytical tool for the trace analysis of diclofenac, which has in the past proved to be an environmental hazard. To this end, a determination limit of 1.2 µg L^–1 could be accomplished, which is thought to be the limit to which it may be harmful to the continental fauna.

References

[1] S. R. Chirasani, P. Leukel, E. Gottfried, J. Hochrein, K. Stadler, B. Neumann, P. J. Oefner, W. Gronwald, U. Bogdahn, P. Hau, M. Kreutz, O. M. Grauer, Int. J. Cancer 2013, 132, 843.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVKlurnP&md5=c50e33ad426a0d36e35b40651de2a329CAS | 22752934PubMed |

[2] P. Forget, C. Bentin, J.-P. Machiels, M. Berliere, P. G. Coulie, M. De Kock, Br. J. Anaesth. 2014, 113, i82.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXht1Clt7jI&md5=f85972aa75ac46000697774042b80172CAS | 24464611PubMed |

[3] (a) H. Krum, G. Swergold, A. Gammaitoni, P. M. Peloso, S. S. Smugar, S. P. Curtis, D. C. Brater, H. Wang, A. Kaur, L. Laine, M. R. Weir, C. P. Cannon, Cardiovasc. Ther. 2012, 30, 342.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtlWnsg%3D%3D&md5=7d9f02f560cb2da734451af99ecbdca2CAS | 21884017PubMed |
      (b) C. Scarpignato, A. Lanas, C. Blandizzi, W. F. Lems, M. Hermann, R. H. Hunt, BMC Med. 2015, 13, 55.
         | Crossref | GoogleScholarGoogle Scholar |

[5] (a) F. Cuklev, E. Kristiansson, J. Fick, N. Asker, L. Förlin, D. G. J. Larsson, Environ. Toxicol. Chem. 2011, 30, 2126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVOlur%2FI&md5=d714f1380aef4517f58af38deb509420CAS | 21688307PubMed |
      (b) F. Gröner, A. Ziková, W. Kloas, Comp. Biochem. Physiol., Part C: Toxicol. Pharmacol. 2015, 167, 51.
         | Crossref | GoogleScholarGoogle Scholar |

[6] J. L. Oaks, M. Gilbert, M. Z. Virani, R. T. Watson, C. U. Meteyer, B. A. Rideout, H. L. Shivaprasad, S. Ahmed, M. J. Chaudhry, M. Arshad, S. Mahmood, A. Ali, A. A. Khan, Nature 2004, 427, 630.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtFCnu7o%3D&md5=87f8349aa217ddb63713c44b27cb26d7CAS | 14745453PubMed |

[7] T. A. Ternes, Water Res. 1998, 32, 3245.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmslaqt7k%3D&md5=8a0c5e2f46e349624f352c82a80d6b8aCAS |

[8] A. Bergmann, R. Fohrmann, F. A. Weber, Zusammenstellung von Monitoringdaten zu Umweltkonzentrationen von Arzneimitteln 2011 (Umweltbundesamt: Dessau-Rosslau).

[9] F. A. Weber, T. aus der Beek, A. Bergmann, A. Carius, G. Grüttner, S. Hickmann, I. Ebert, A. Hein, A. Küster, J. Rose, J. Koch-Jugl, H. C. Stolzenberg, Pharmaceuticals in the Environment – The Global Perspective 2014 (IWW Rheinisch-Westfaelisches Institut für Wasser Beratungs- und Entwicklungsgesellschaft mbH: Muelheim). Available at: http://www.pharmaceuticals-in-the-environment.org (accessed 15 March 2015).

[10] M. Meißner, Dtsch. Arztebl. Int. 2008, 105, 1324.

[11] (a) M. Hilder, P. C. Junk, U. H. Kynast, M. M. Lezhnina, J. Photochem. Photobiol. Chem. 2009, 202, 10.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpsF2jtA%3D%3D&md5=703c31841d3dc22f64affde112f8c5deCAS |
      (b) M. Hilder, M. Lezhnina, M. L. Cole, C. M. Forsyth, P. C. Junk, U. H. Kynast, J. Photochem. Photobiol. Chem. 2011, 217, 76.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Hilder, M. Lezhnina, P. C. Junk, U. H. Kynast, Polyhedron 2013, 52, 804.
         | Crossref | GoogleScholarGoogle Scholar |

[12] (a) B. Yan, H. J. Zhang, S. B. Wang, J. Z. Ni, Monatsh. Chem. 1998, 129, 151.
         | 1:CAS:528:DyaK1cXhtlWgs7s%3D&md5=fa5168d555733b58a4942ce0d23ea10eCAS |
      (b) Z. M. Wang, L. J. van de Burgt, G. R. Choppin, Inorg. Chim. Acta 1999, 293, 167.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) V. Tsaryuk, K. Zhuravlev, V. Zolin, P. Gawryszewska, J. Legendziewicz, V. Kudryashova, I. Pekareva, J. Photochem. Photobiol. Chem. 2006, 177, 314.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. de Bettencourt-Dias, P. S. Barber, S. Viswanathan, Coord. Chem. Rev. 2014, 273–274, 165.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) E. Rezende Souza, I. G. N. Silva, E. E. S. Teotonio, M. C. F. C. Felinto, H. F. Brito, J. Lumin. 2010, 130, 283.
         | Crossref | GoogleScholarGoogle Scholar |

[13] (a) O. V. Kotova, S. V. Eliseeva, A. A. Volosnikov, V. A. Oleinikov, L. S. Lepnev, A. G. Vitukhnovskii, N. P. Kuzmina, Russ. J. Coord. Chem. 2006, 32, 901.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht12qtbvK&md5=be791a8733fb558cddb05b6feb3370d5CAS |
      (b) T. Fiedler, M. Hilder, P. C. Junk, U. H. Kynast, M. M. Lezhnina, M. Warzala, Eur. J. Inorg. Chem. 2007, 291.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) T. H. Tran, M. M. Lezhnina, U. Kynast, J. Mater. Chem. 2011, 21, 12819.
         | Crossref | GoogleScholarGoogle Scholar |

[14] (a) D. Sendor, P. Junk, U. Kynast, Solid State Phenom. 2003, 90–91, 521.
| Crossref | GoogleScholarGoogle Scholar |
(b) D. Sendor, U. Kynast, in Host-Guest Systems Based on Nanoporous Crystals (Eds F. Laeri, F. Schüth, U. Simon, M. Wark) 2003, pp. 558–583 (Wiley-VCH: Weinheim).

[15] (a) S. Sato, M. Wada, Bull. Chem. Soc. Jpn. 1970, 43, 1955.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXkvVags7Y%3D&md5=33259544626a04a03c1aba19cf24ea08CAS |
      (b) A. M. De Andrade, N. Da Costa, R. Longo, O. Malta, A. Simas, G. De Sá, Mol. Eng. 1997, 7, 293.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Yan, H. Zhang, S. Wang, J. Ni, J. Photochem. Photobiol. Chem. 1998, 116, 209.
         | Crossref | GoogleScholarGoogle Scholar |

[16] O. I. Teslyuk, S. V. Bel’tyukova, A. V. Yegorova, B. N. Yagodkin, J. Anal. Chem. 2007, 62, 330.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXktVehur4%3D&md5=8eee0135522efd0f0d9872bb76359115CAS |

[17] (a) R. Bucci, A. D. Magrì, A. L. Magrì, Fresenius’ J. Anal. Chem. 1998, 362, 577.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXnvFWnsLo%3D&md5=d5f072933045850393ffee716d487e45CAS |
      (b) M. Bartolomei, P. Bertocchi, E. Antoniella, A. Rodomonte, J. Pharm. Biomed. Anal. 2006, 40, 1105.
         | Crossref | GoogleScholarGoogle Scholar |

[18] (a) W. F. Sager, N. Filipescu, F. A. Serafin, J. Phys. Chem. 1965, 69, 1092.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2MXntFWksw%3D%3D&md5=65815d002cdd0ea1ab7f6bf7791a07afCAS |
      (b) M. Latva, H. Takalo, V.-M. Mukkala, C. Matachescu, J. C. Rodriguez-Ubis, J. Kankare, J. Lumin. 1997, 75, 149.
         | Crossref | GoogleScholarGoogle Scholar |

[19] G. H. Dieke, Spectra and Energy Levels of Rare Earth Ions in Crystals 1968 (Interscience Publishers: New York, NY).

[20] M. D. Regulacio, M. H. Pablico, J. A. Vasquez, P. N. Myers, S. Gentry, M. Prushan, S. W. Tam-Chang, S. L. Stoll, Inorg. Chem. 2008, 47, 1512.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsV2gu7s%3D&md5=9bcb7d0b02f60419f05ea953fbb2b1dcCAS | 18247543PubMed |

[21] (a) L. N. Puntus, K. A. Lyssenko, M. Y. Antipin, J.-C. G. Bünzli, Inorg. Chem. 2008, 47, 11095.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlSntbnJ&md5=9af29118644f7c690950fecaa61393a6CAS | 18950154PubMed |
      (b) L. N. Puntus, K. A. Lyssenko, I. S. Pekareva, J.-C. G. Bünzli, J. Phys. Chem. B 2009, 113, 9265.
         | Crossref | GoogleScholarGoogle Scholar |

[22] (a) F. R. G. e Silva, J. F. S. Menezes, G. B. Rocha, S. Alves, H. F. Brito, R. L. Longo, O. L. Malta, J. Alloys Compd. 2000, 303–304, 364.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) M. M. Lezhnina, D. Hofmann, B. Santiago-Schuebel, P. Klauth, U. H. Kynast, New J. Chem. 2012, 36, 2322.
         | Crossref | GoogleScholarGoogle Scholar |

[23] C. F. de Souza, R. K. S. Martins, A. R. da Silva, A. L. M. C. da Cunha, R. Q. Aucélio, Spectrochim. Acta, Part A 2013, 100, 51.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xhs12hsrfM&md5=35d1860628fb4743b3ec29d2db66f14eCAS |

[24] T. H. Tran, M. Bentlage, M. M. Lezhnina, U. Kynast, J. Photochem. Photobiol. Chem. 2014, 273, 43.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslWlt7zP&md5=918885a4f701a5f6c4a841a86943afdfCAS |

[25] T. Felbeck, M. M. Lezhnina, U. Resch-Genger, U. H. Kynast, J. Lumin. 2014,
| Crossref | GoogleScholarGoogle Scholar |

Photophysical Properties of Rare Earth Diclofenac Complexes in the Solid State

Abstract

References

Subscriber Login