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Synthesis, X-Ray Crystal Structures and Optical Properties of Novel Substituted Pyrazoly 1,3,4-Oxadiazole Derivatives

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Abstract

Novel pyrazoly 1,3,4-oxadiazole derivatives were synthesized and characterized by 1H NMR, IR, HRMS and X-ray diffraction analysis. UV–vis absorption and fluorescence properties of these compounds in different solutions showed that the maximum absorption wavelength was not significantly changed in different solvents; however, maximal emission wavelength was red-shifted with the increase of solvent polarity. Absorption λmax and emission λmax was less correlated with substituent groups on aryl rings.

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References

  1. Guan M, Bian ZQ, Zhou YF, Li FY, Li ZJ, Huang CH (2003) High-performance blue electroluminescent devices based on 2-(4-biphenylyl) -5-(4-carbazole-9- yl)phenyl-1,3,4- oxadiazole. Chem Commun:2708–2709

  2. Hughes G, Bryce MR (2005) Electron-transporting materials for organic electroluminescent and electrophosphorescent devices. J Mater Chem 15:94–107

    Article  CAS  Google Scholar 

  3. Zhu YC, He DH, Yang ZR (2009) Synthesis and optical properties of two novel stilbene derivatives containing 1,3,4-oxadiazole moiety. Spectrochim Acta A 72:417–420

    Article  Google Scholar 

  4. Tao YT, Wang CL, Wang Q, Zhang ZQ, Zou TT, Qin JG, Ma DG (2008) A simple carbazole/oxadiazole hybrid molecule: an excellent bipolar host for green and red phosphorescent OLEDs. Angew Chem Int Edit 47:8104–8107

    Article  CAS  Google Scholar 

  5. Tao YT, Wang Q, Shang Y, Yang CL, Ao L, Qin JG, Ma DG, Shuai ZG (2009) Multifunctional bipolar triphenylamine/oxadiazole derivatives: highly efficient blue fluorescence, red phosphorescence host and two-color based white OLEDs. Chem Commun:77–79

  6. Kaminorz Y, Schulz B, Schrader S, Brehmer L (2001) OLEDs based on new oxadiazole derivatives. Synth Met 122:115–118

    Article  CAS  Google Scholar 

  7. Lv ZY, Deng ZB, Zheng JJ, Xu DH, Chen Z, Zhou EY, Wang YS (2010) Organic light-emitting diodes with 2-(4-biphenylyl)-5(4-tert-butyl-phenyl)-1,3,4-oxadiazole layer inserted between hole-injecting and hole-transporting layers. Vacuum 84:1287–1290

    Article  Google Scholar 

  8. Chen HY, Chen CT, Chen CT (2010) Synthesis and characterization of a new series of blue fluorescent 2,6-linked 9,10-diphenylanthrylenephenylene copolymers and their application for polymer light-emitting diodes. Macromolecules 43:3613–3623

    Article  CAS  Google Scholar 

  9. Manjunatha MG, Adhikari AV, Hegde PK, Sandeep CSS, Philip R (2010) Synthesis and characterization of a new NLO-active donor–acceptor-type conjugated polymer derived from 3,4-diphenylthiophene. J Polym Res 17:495–502

    Article  CAS  Google Scholar 

  10. Liu CB, Li J, Li B, Hong ZR, Zhao FF, Liu SY, Li WL (2007) A multicomponent rhenium-based triplet emitter for organic electroluminescence. Chem Phys Lett 435:54–58

    Article  CAS  Google Scholar 

  11. He Z, Wong WY, Yu XM, Kwok HS, Lin ZY (2006) Phosphorescent platinum (II) complexes derived from multifunctional chromophores: synthesis, structures, photophysics, and electroluminescence. Inorg Chem 45:10922–10937

    Article  PubMed  CAS  Google Scholar 

  12. Chen LQ, Yang CL, Qin JG, Gao J, You H, Ma DG (2006) Synthesis, structure, electrochemistry, photophysics and electroluminescence of 1,3,4-oxadiazole-based ortho-metalated iridium(III) complexes. J Organomet Chem 691:3519–3530

    Article  CAS  Google Scholar 

  13. Si ZJ, Li J, Li B, Zhao FF, Liu SY, Li WL (2007) Synthesis, structural characterization, and electrophosphorescent properties of rhenium (I) complexes containing carrier-transporting groups. Inorg Chem 46:6155–6163

    Article  PubMed  CAS  Google Scholar 

  14. Xu ZW, Li Y, Ma XM, Gao XD, Tian H (2008) Synthesis and properties of iridium complexes based 1,3,4-oxadiazoles derivatives. Tetrahedron 64:1860–1867

    Article  CAS  Google Scholar 

  15. Moret ME, Chen P (2010) Mononuclear platinum (II) complexes of a bis(bidentate) ligand based on 1,3,4-oxadiazole and their reactions with copper (I) salts. Eur J Inorg Chem 2010:438–446

    Article  Google Scholar 

  16. Han J, Wei YH (2010) Synthesis, single crystal structure and photo-luminescent property of bipolar compounds containing 1,3,4-oxadiazole and carbazolyl units. J Mol Struct 968:32–35

    Article  CAS  Google Scholar 

  17. Wang G, He Y (2009) New oxadiazole complex with bipolar ligand for organic light-emitting devices. Mater Lett 63:470–472

    Article  CAS  Google Scholar 

  18. Li AF, Ruan YB, Jiang QQ, He WB, Jiang YB (2010) Molecular logic gates and switches based on 1,3,4-oxadiazoles triggered by metal ions. Chem Eur J 16:5794–5802

    CAS  Google Scholar 

  19. Wang CS, Jung GY, Batsanov AS, Bryce MR, Petty MC (2002) New electron-transporting materials for light emitting diodes: 1,3,4-oxadiazole–pyridine and 1,3,4-oxadiazole–pyrimidine hybrids. J Mater Chem 12:173–180

    Article  CAS  Google Scholar 

  20. Chien YY, Wong KT, Chou PT, Cheng YM (2002) Syntheses and spectroscopic studies of spirobifluorene-bridged bipolar systems; photoinduced electron transfer reactions. Chem Commun:2874–2875

  21. Bhandari SV, Bothara KG, Raut MK, Patil AA, Sarkate AP, Mokale VJ (2008) Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel s-substituted phenacyl-1,3,4-oxadiazole-2-thiol and schiff bases of diclofenac acid as nonulcerogenic derivatives. Bioorg Med Chem 16:1822–1831

    Article  PubMed  CAS  Google Scholar 

  22. Kumar D, Sundaree S, Johnson EO, Shah K (2009) An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents. Bioorg Med Chem Lett 19:4492–4494

    Article  PubMed  CAS  Google Scholar 

  23. Kumar A, D’Souza SS, Gaonkar SL, Rai KM, Salimath BP (2008) Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by a new series of substituted-1,3,4-oxadiazole derivatives. Invest New Drugs 26:425–435

    Article  PubMed  CAS  Google Scholar 

  24. Rai NP, Narayanaswamy VK, Shashikanth S, Arunachalam PN (2009) Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl) -5-methyl-1 H-pyrazol-4-yl]-5-(substituted-phenyl)-[1, 3, 4]oxadiazoles. Eur J Med Chem 44:4522–4527

    Article  PubMed  CAS  Google Scholar 

  25. Chandrakantha B, Shetty P, Nambiyar V, Isloor N, Isloor AM (2010) Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety. Eur J Med Chem 45:1206–1210

    Article  PubMed  CAS  Google Scholar 

  26. Lv HS, Zhao BX, Li JK, Xia Y, Lian S, Liu WY, Gong ZL (2010) The synthesis, characterization and optical properties of novel, substituted, pyrazoly 1,3,4-oxadiazole derivatives. Dyes and Pigments 86:25–31

    Article  CAS  Google Scholar 

  27. Xia Y, Dong ZW, Zhao BX, Ge X, Meng N, Shin DS, Miao JY (2007) Synthesis and structure–activity relationships of novel 1-arylmethyl-3-aryl-1 H-pyrazole −5-carbohydrazide derivatives as potential agents against A549 lung cancer cells. Bioorg Med Chem 15:6893–6899

    Article  PubMed  CAS  Google Scholar 

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Acknowledgement

This study was supported by National Natural Science Foundation of China (90813022 and 20972088) and the Science and Technology Developmental Project of Shandong Province (2008GG10002034).

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Authors and Affiliations

  1. Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, People’s Republic of China

    Hong-Shui Lv, Wei-Yong Liu, Zhong-Liang Gong & Bao-Xiang Zhao

  2. Department of Chemical and Environment Engineering, Chongqing Three Gorges University, Chongqing, 404000, People’s Republic of China

    Yong-Sheng Xie

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  1. Hong-Shui Lv
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  2. Yong-Sheng Xie
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Correspondence to Bao-Xiang Zhao.

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10895_2011_874_MOESM1_ESM.doc

CCDC 787253 and 787254 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 1223336033. (DOC 24 kb)

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Lv, HS., Xie, YS., Liu, WY. et al. Synthesis, X-Ray Crystal Structures and Optical Properties of Novel Substituted Pyrazoly 1,3,4-Oxadiazole Derivatives. J Fluoresc 21, 1797–1804 (2011). https://doi.org/10.1007/s10895-011-0874-7

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