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Synthesis, Characterization and Properties of Novel Coumarin Derivatives and Their Europium Complexes

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Abstract

Seven novel coumarin derivatives derived from salicylaldehyde and phenol were synthesized and characterized by 1H NMR and 13C NMR spectra, mass spectra, infrared spectra and elemental analysis. Their corresponding Eu(III) complexes having general formula EuL1−7(NO3)3⋅2H2O were successfully prepared and characterized by elemental analysis, EDTA titrimetric, molar conductivity, UV–Vis, FT-IR and thermal performance studies. The luminescence properties, fluorescence quantum yields and the electrochemical properties of the title complexes were investigated. The results showed that the title complexes exhibited characteristic emissions of europium ions and possessed relatively good fluorescence quantum yields. The luminescence intensity of the complex with bromine-substituted group is the strongest among all the title complexes. The introduction of electron-withdrawing groups can increase the luminescence properties and fluorescence quantum yields, decrease the HOMO and LUMO energy levels of the title europium complexes, but electron-withdrawing group conversely. And these title complexes may possibly be useful for studying in luminescent materials field.

Synthesis route of the ligands L 1−7

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References

  1. Zhou J, Lu ZG, Shan GG, Wang SH, Liao Y (2014) Gadolinium complex and phosphorescent probe-modified NaDyF4 nanorods for T1-and T2-weighted MRI/CT/phosphorescence multimodality imaging. Biomaterials 35:368–377

    Article  CAS  PubMed  Google Scholar 

  2. Mishra A, Fouskova P, Angelovski G, Balogh E, Mishra AK, Logothetis NK, Tóth É (2008) Facile synthesis and relaxation properties of novel bispolyazamacrocyclic Gd3+ complexes: an attempt towards calcium-sensitive MRI contrast agents. Inorg Chem 47:1370–1381

    Article  CAS  PubMed  Google Scholar 

  3. Feng J, Zhang HJ (2013) Hybrid materials based on lanthanide organic complexes: a review. Chem Soc Rev 42:387–410

    Article  CAS  PubMed  Google Scholar 

  4. Suzuki H, Hattori Y, Iizuka T, Yuzawa K, Matsumoto N (2003) Organic infrared optical materials and devices based on an organic rare earth complex. Thin Solid Films 438:288–293

    Article  Google Scholar 

  5. Wei HB, Yu G, Zhao ZF, Liu ZW, Bian ZQ, Huang CH (2013) Constructing lanthanide [Nd (III), Er (III) and Yb (III)] complexes using a tridentate N, N, O-ligand for near-infrared organic light-emitting diodes. Dalton Trans 42:8951–8960

    Article  CAS  PubMed  Google Scholar 

  6. Oyamada T, Kawamura Y, Koyama T, Sasabe H, Adachi C (2004) Formation of europium chelate complexes by vacuum co-deposition and their application in organic light-emitting diodes. Adv Mater 16:1082–1086

    Article  CAS  Google Scholar 

  7. Wang Y, Ji L, Zhang B, Yin P, Qiu Y, Song D, Zhou J, Li Q (2013) Upconverting rare-earth nanoparticles with a paramagnetic lanthanide complex shell for upconversion fluorescent and magnetic resonance dual-modality imaging. Nanotechnology 24:175101

    Article  PubMed  Google Scholar 

  8. Yang CL, Xu J, Li JY, Lu MG, Li YB, Wang XL (2014) An efficiently colorimetric and fluorescent probe of fluoride, acetate and phosphate ions based on a novel trinuclear Eu-complex. Sensors Actuators B Chem 196:133–139

    Article  CAS  Google Scholar 

  9. Sun LN, Zhang HJ, Meng QG, Liu FY, Fu LS, Peng CY, Yu JB, Zheng GL, Wang SB (2005) Near-infrared luminescent hybrid materials doped with lanthanide (Ln) complexes (Ln = Nd, Yb) and their possible laser application. J Phys Chem B 109:6174–6182

    Article  CAS  PubMed  Google Scholar 

  10. Wang W, Huang Y, Tang N (2007) Synthesis and infrared and fluorescence spectra of rare earth complexes with a novel amide-based ligand. Spectrochim Acta A 66:1058–1062

    Article  Google Scholar 

  11. Yadav P, Satapathi S, Kumari M, Chaturvedi A, Li L, Samuelson LA, Kumar J, Sharma SK (2014) Synthesis of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization. J Photochem Photobiol A Chem 280:39–45

    Article  CAS  Google Scholar 

  12. Amin KM, Abdel Gawad NM, Abdel Rahman DE, el Ashry MKM (2014) New series of 6-substituted coumarin derivatives as effective factor Xa inhibitors: Synthesis, in vivo antithrombotic evaluation and molecular docking. Bioorg Chem 52:31–43

    Article  CAS  PubMed  Google Scholar 

  13. Mahapatra AK, Hazra G, Roy J, Sahoo P (2011) A simple coumarin-based colorimetric and ratiometric chemosensor for acetate and a selective fluorescence turn-on probe for iodide. J Lumin 131:1255–1259

    Article  CAS  Google Scholar 

  14. Nakagawa K, Amita K, Mizuno H, Inoue Y, Hakushi T (1987) Preparation of some lanthanoid picrates and the behavior of their water of hydration. Bull Chem Soc Jpn 60:2037

    Article  CAS  Google Scholar 

  15. Li J, Li X, Wang S (2012) Synthesis, photoluminescent behaviors, and theoretical studies of two novel ketocoumarin derivatives. Spectrochim Acta, Part A 88:31–36

    Article  CAS  Google Scholar 

  16. Geary WJ (1971) The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev 7:81–122

    Article  CAS  Google Scholar 

  17. Feigenbrugel V, Loew C, Calve TL, Mirabel P (2005) Near-UV molar absorptivities of acetone, alachlor, metolachlor, diazinon and dichlorvos in aqueous solution. J Photochem Photobiol A Chem 174:76–81

    Article  CAS  Google Scholar 

  18. Gansow OA, Loeffler PA, Davis RE, Lenkinski RE, Wilcott MR (1976) Contact vs. pseudocontact contributions to lanthanide-induced shifts in the nuclear magnetic resonance spectra of isoquinoline and of endo-norbornenol. J Am Chem Soc 14:4250–4258

    Article  Google Scholar 

  19. Taha ZA, Ajlouni AM, Al-Hassan KA, Hijazi AK, Faiq AB (2011) Syntheses, characterization, biological activity and fluorescence properties of bis- (salicylaldehyde)-1, 3-propylenediimine Schiff base ligand and its lanthanide complexes. Spectrochim Acta A 81:317–323

    Article  CAS  Google Scholar 

  20. Kai K, Zhang HX, Ma RJ, Chen YN, Chu HB, Zhao YL (2013) Synthesis, characterization and enhanced luminescence of terbium complexes with 2-pyrazinecarboxylic acid and butanedioic acid by inert-fluorescent lanthanide ions. J Rare Earths 31:32–36

    Article  Google Scholar 

  21. Tian L, Ren N, Zhang JJ, Liu HM, Bai JH, Ye HM, Sun SJ (2009) Synthesis, crystal structure, luminescence and thermal decomposition kinetics of Eu (III) complex with 2, 4-dichlorobenzoic acid and 2, 2′-bipyridine. Inorg Chim Acta 362:3388–3394

    Article  CAS  Google Scholar 

  22. Guo DC, He W, Liu B, Gou LN, Li RX (2013) Synthesis and luminescence properties of 2-(benzylcarbamoyl) phenyl derivatives and their europium complexes. Luminescence 28:280–286

    Article  CAS  PubMed  Google Scholar 

  23. Kirby AF, Richardson FS (1983) Detailed analysis of the optical absorption and emission spectra of europium (3+) in the trigonal (C3) Eu(DBM)3⋅H2O system. J Phys Chem 87:2544–2556

    Article  CAS  Google Scholar 

  24. Li WX, Li YJ, Chai WJ, Ren T, Liu Y, Zhang J, Ao BY (2012) Syntheses and fluorescence properties of two novel lanthanide (III) perchlorate complexes with bis (benzylsulfinyl) methane. J Fluoresc 22:651–658

    Article  CAS  PubMed  Google Scholar 

  25. Guo DC, Wu PL, Tan H, Xia L, Zhou WH (2011) Synthesis and luminescence properties of novel 4-(N-carbazole methyl) benzoyl hydrazone Schiff bases. J Lumin 131:1272–1276

    Article  CAS  Google Scholar 

  26. Ding BD, Zhang JM, Zhu WQ et al (2002) Fast and convenient determination of HOMO energy level of organic electroluminescent material using electrochemistry method. Chem Res Appl 14:712–714

    CAS  Google Scholar 

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Acknowledgments

The authors are grateful for the financial support of the National Natural Science Foundation of China (No.J1103312; No.J1210040; No.21341010), the Innovative Research Team in University (No.IRT1238) and chemical excellent engineer training program of Hunan university. We also thank Dr. William Hickey, the U.S. professor of HRM, for the English editing on this paper.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China

    Dong Yan, Dong Li, Guang Cheng, Ling Shi & Dongcai Guo

  2. School of Chemical Engineering, Ningbo University of Technology, Ningbo, 315016, China

    Zehui Yang

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  1. Dong Yan
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  2. Dong Li
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  3. Guang Cheng
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  5. Ling Shi
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Correspondence to Dongcai Guo.

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Yan, D., Li, D., Cheng, G. et al. Synthesis, Characterization and Properties of Novel Coumarin Derivatives and Their Europium Complexes. J Fluoresc 25, 849–859 (2015). https://doi.org/10.1007/s10895-015-1563-8

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  • DOI: https://doi.org/10.1007/s10895-015-1563-8

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