A new calix[4]azacrown ether based boradiazaindacene (Bodipy): Selective fluorescence changes towards trivalent lanthanide ions

Dyes and Pigments

Volumn 99, Issue 2, 2013, Pages 268-274

  Bayrakci, Mevlüt ^a   Kursunlu, Ahmed Nuri ^b   Güler, Ersin ^b   Ertul, Şeref ^b  

^a NIGDE UNIVERSITY   (Turkey)

^b SELCUK UNIVERSITY   (Turkey)

Author keywords

Bodipy; Calixcrown; Fluorescence probe; Lanthanide ions; Recognition Chemosensor

Indexed keywords

BODIPY; CALIX-CROWN; CHEMOSENSOR; FLUORESCENCE PROBES; LANTHANIDE ION;

AMIDES; BINDING ENERGY; ETHERS; FLUORESCENCE; IONS;

YTTERBIUM;

EID: 84879197974     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.05.025     Document Type: Article

References (45)

1. Z. Zhang, B. Xu, J. Su, L. Shen, Y. Xie, and H. Tian Color-tunable solid-state emission of 2,2′-biindenyl-based fluorophores Angew Chem Int Ed 50 2011 11654 11657
2. V. Csokai, M. Kadar, D.L.H. Mai, O. Varga, K. Toth, and M. Kubinyi Synthesis, optical and electroanalytical characterizations of a thiacalix[4](N-phenylazacrown-5)ether-BODIPY ionophore Tetrahedron 64 2008 1058 1063 (Pubitemid 350266751)
3. S. Hirano, and K.T. Suzuki Exposure, metabolism, and toxicity of rare earths and related compounds Environ Health Perspect 104 1996 85 95 (Pubitemid 26123094)
4. H.J. Kim, and J.S. Kim BODIPY appended cone-calix[4]arene: selective fluorescence changes upon CaÂ+ binding Tetrahedron Lett 47 2006 7051 7055 (Pubitemid 44425257)
5. Z. Liu, L. Jiang, Z. Liang, and Y. Gao A selective colorimetric chemosensor for lanthanide ions Tetrahedron 62 2006 3214 3220
6. V.M. Mukkala, M. Helenius, I. Hemmila, J. Kankare, and H. Takalo Development of luminescent europium-(III) and terbium(III) chelates of 2,2,60,20-terpyridine derivatives for protein labeling Helv Chim Acta 76 1992 1361 1378
7. H. Mikola, H. Takalo, and I. Hemmila Syntheses and properties of luminescent lanthanide chelate labels and labeled haptenic antigens for homogeneous immunoassays Bioconjug Chem 6 1995 235 241
8. T. Gunnlaugsson, and J.P. Leonard Responsive lanthanide luminescent cyclen complexes: from switching/sensing to supramolecular architectures Chem Commun 2005 3114 3131 (Pubitemid 41002372)
9. M. Remuinan, H. Roman, M. Alonso, and J. RodrIguez-Ubis Synthesis and luminiscence properties of europium(III) and terbium(III) complexes with polyacid chelates derived from 2,6-bis(N-pyrazolyl)pyridine J Chem Soc Perkin Trans 2 1993 1099 1102
10. 3+-cryptates of polypyridine macrobicyclic ligands Angew Chem Int Ed Engl 26 1987 2264
11. C.N. Baki, and E.U. Akkaya Boradiazaindacene-appended calix[4]arene: fluorescence sensing of pH near neutrality J Org Chem 66 2001 1512 1513 (Pubitemid 32202342)
12. Z. Pikramenou, and D.G. Nocera Luminescent supramolecular architectures- a cyclodextrin modified with a europium(III) crown swing Inorg Chem 31 1992 532 536
13. N. Sabbatini, S. Dellonte, and G. Blasse The luminescence of the rare-earth cryptates [tb-subset-of-2.2.1]3+ and [sm-subset-of-2.2.1]3+ Chem Phys Lett 129 1986 541 545
14. M.L. Metzker, J. Lu, and R.A. Gibbs Electrophoretically uniform fluorescent dyes for automated DNA sequencing Science 271 1996 1420 1422 (Pubitemid 26089478)
15. S.Y. Moon, N.R. Cha, Y.H. Kim, and S.K. Chang New Hg2+-selective chromo-and fluoroionophore based upon 8-hydroxyquinoline J Org Chem 69 2004 181 183 (Pubitemid 38040823)
16. S. Erten-Ela, M.D. Yilmaz, B. Icli, Y. Dede, S. Icli, and E.U. Akkaya A panchromatic boradiazaindacene (BODIPY) sensitizer for dye-sensitized solar cells Org Lett 10 2008 3299 3302
17. G. Barin, D.Y. Yilmaz, and E.U. Akkaya Boradiazaindacene (Bodipy)-based building blocks for the construction of energy transfer cassettes Tetrahedron Lett 50 2009 1738 1740
18. R. Guliyev, S. Ozturk, Z. Kostereli, and E.U. Akkaya From virtual to physical: integration of chemical logic gates Angew Chem Intl Ed Engl 50 2011 9826 9831
19. C.D. Gutche Calixarenes, revisited; the royal society of chemistry: cambridge, 1998 J. Vicens, V. Boehmer, Calixarenes: a versatile class of macrocyclic compounds 1991 Kluwer Academic Boston
20. C.D. Gutsche, M. Iqbal, and D. Stewart Calixarenes.18. synthesis procedures for para-tert-butylcalix[4]arene J Org Chem 51 1986 742 745
21. C.D. Gutsche, B. Dhawan, K.H. No, and R. Muthukrishnan Calixarenes.4. The synthesis, characterization, and properties of the calixarenes from para-tert-butylphenol J Am Chem Soc 103 1981 3782 3792
22. H. Chen, Y.S. Gal, S.H. Kim, H.J. Choi, M.C. Oh, and J. Lee Potassium ion sensing using a self-assembled calix[4]crown monolayer by surface plasmon resonance Sensor Actuators B 133 2008 577 581
23. M. Bayrakci, S. Ertul, and M. Yilmaz Synthesis of di-substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions Tetrahedron 65 2009 7963 7968
24. M. BayrakcI, S. Ertul, and M. Yilmaz Transportation of poorly soluble drug molecules from the organic phase to the aqueous phase by using phosphorylated calixarenes J Chem Eng Data 56 2011 4473 4479
25. M. BayrakcI, S. Ertul, and M. Yilmaz Phase solubility studies of poorly soluble drug molecules by using O-phosphorylated calixarenes as drug-solubilizing agents J Chem Eng Data 57 2012 233 239
26. M. BayrakcI, S. Ertul, and M. Yilmaz Solubilizing effect of the p-phosphonate calix[n]arenes towards poorly soluble drug molecules such as nifedipine, niclosamide and furosemide J Incl Phenom Macrocycl Chem 74 2012 415 423
27. C.D. Gutsche, and I. Alam Calixarenes. 23. The complexation and catalytic properties of water-soluble calixarenes Tetrahedron 44 1988 4689 4694
28. A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, and R. Ungaro Sugar calixarenes - preparation of calix[4]arenes substituted at the lower and upper rims with o-glycosyl groups Angew Chem Intl Ed Engl 33 1995 2479 2481 (Pubitemid 24977333)
29. A. Ikeda, and S. Shinkai Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding Chem Rev 97 1997 1713 1734 (Pubitemid 127659611)
30. C. Alfieri, E. Dradi, A. Pochini, R. Ungaro, and G.D. Andreetti Synthesis, and x-ray crystal and molecular-structure of a novel macrobicyclic ligand-crowned para-tert-butyl-calix[4]arene J Chem Soc Chem Commun 1983 1075 1077
31. I. Oueslati Calix(aza)crowns: synthesis, recognition, and coordination. A mini review Tetrahedron 63 2007 10840 10851
32. Y.M. Jeon, B.H. Kim, J.G. Kim, M.S. Gong, and J.G. Jang Preparation of blue anthracene fluoroionophore containing calix[4]azacrown and their luminescent properties Macromol Res 14 2006 663 667
33. S.H. Kim, C.V. Lee, and M.S. Gong Synthesis and properties of calix[4]crown-6 functionalized polymers Macromol Res 13 2005 141 146
34. P.D. Beer, G.D. Brindley, O.D. Fox, A. Grieve, M.I. Ogden, and F. Szemes Acid-amide calixarene ligands for uranyl and lanthanide ions: synthesis, structure, coordination and extraction studies J Chem Soc Dalton Trans 2002 3101 3111 (Pubitemid 35202169)
35. I. Oueslati, R.A. Ferreira, L.D. Carlos, C. Baleiza, M.N. Berberan-Santos, and B. de Castro Calix[4]azacrowns as novel molecular scaffolds for the generation of visible and near-infrared lanthanide luminescence Inorg Chem 45 2006 2652 2660
36. R. Ostaszewski, T.W. Stevens, W. Verboom, D.N. Reinhoudt, and F.M. Kaspersen Calix(aza)crowns as potential ionophores for divalent and trivalent cations Recl Trav Chim Pays-Bas 110 1991 294 298
37. I. Garcia-Moreno, A. Costela, L. Campo, R. Sastre, F. Amat-Guerri, and M. Liras 8-phenyl-substituted dipyrromethene center dot BF2 complexes as highly efficient and photostable laser dyes J Phys Chem A 108 2004 3315 3323
38. J.C.G. Bünzli, and C. Piguet Taking advantage of luminescent lanthanide ions Chem Soc Rev 34 2005 1048 1077 (Pubitemid 41805039)
39. Y. Zhong, L. Si, H. He, and A.G. Sykes BODIPY chromophores as efficient green light sensitizers for lanthanide-induced near-infrared emission Dalton Trans 40 2011 11389 11395
40. R. Ebdelli, A. Rouis, R. Mlika, I. Bonnamour, H.B. Ouada, and J. Davenas Photo-physical and complexation properties of chromogenic azo-calix[4]arene: application to the detection of Eu3+ J Mol Struc 1006 2011 210 215
41. Z. Liang, Z. Liu, and Y. Gao A selective colorimetric chemosensor based on calixarene framework for lanthanide ions-Dy3+ and Er3+ Tetrahedron Lett 48 2007 3587 3590 (Pubitemid 46590185)
42. H.-J. Zhang, G. Li, L. Yan, and R.-D. Yang Synthesis, characterization and luminescence properties of N, N′-bis(2 - pyridinecarboxamide-1-N- oxide)-1,2-ethane and corresponding lanthanide (III) complexes J Lumin 127 2007 316 320 (Pubitemid 47238849)
43. N. Cheriaa, R. Abidi, and J. Vicens Synthesis and complexing properties of four imidazolyl acetamido p-tert-butylcalix[4]arenes J Incl Phenom Macrocycl Chem 60 2008 303 312
44. O.,V. Snurnikova, A.P. Lukyanenko, E.A. Alekseeva, Y.V. Korovin, and N.V. Rusakova Synthesis and spectral-luminescent properties of polynuclear lanthanide complexes with functionalized calix[4]arenes Macroheterocycles 4 2011 93 96
45. R.G. Pearson, and T.L. Ho Hard soft acids bases (HSAB) principle and organic chemistry Chem Rev 75 1975 1 20