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Synthesis, Characterization and Photophysical Properties of Novel Azole Derivatives

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Abstract

This paper concerns the design, synthesis, structural characterization, thermal stability evaluation and fluorescence properties of novel triazolothiadiazole derivatives. The target compounds 6a–e were synthesized by condensing 4-amino-3-(4-methoxybenzyl)-1H-1,2,4-triazole-5 (4H)-thione (5) with biphenyl, naphthyl, p-terphenyl, pyrenyl and ferrocenyl carboxylic acid in the presence of phosphorous oxychloride. The structures of newly synthesized compounds were characterized by IR,1H NMR and 13C NMR analysis. The photophysical properties of synthesized compounds were measured in a variety of organic solvents of variable polarities. Spectral properties of the compounds were highly dependent on the nature of the substituent and coupling components attached to the triazolothiadiazole skeleton as well as slightly affected by the solvent polarities. Correlation of the absorption spectra and fluorescence emission response of 6a–e with the substituent revealed that the fluorescent properties can easily be tuned by varying conjugation length of side coupled groups. The newly synthesized derivatives represent a new type of fluorescent materials with efficient visible absorption and surpassing brightness which could be a promising candidate for bioimaging, photonic applications, organic light emitting diodes and dye sensitized solar cells.

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References

  1. Patilj VS, Padalkar VS, Tathe AB, Gupta VD, Sekar J (2013) Synthesis, photo-physical and DFT studies of ESIPT inspired novel 2-(2′,4′-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole. J Fluoresc 23:1019–1029

    Article  Google Scholar 

  2. Gulcan M, Dogru U, Ozturk G, Levent A, Akbas E (2014) Fluorescence properties and electrochemical behavior of some schiff bases derived from N-aminopyrimidine. J Fluoresc 24:389–396

    Article  CAS  Google Scholar 

  3. Ahmed KS, El-Molla MM, Abdel-Mottaleb MSA, Attia MS, El-Saadany S (2013) Synthesis and evaluation of novel fluorescent dyes using microwave irradiation. Res J Chem Sci 3:3–18

    CAS  Google Scholar 

  4. Yu T, Zhang C, Zhao Y, Guo SQ, Liu P, Li W, Fan D (2013) Synthesis, crystal structure and photoluminescence of a cyclometalated Iridium(III) coumarin complex. J Fluoresc 23:777–783

    Article  CAS  PubMed  Google Scholar 

  5. Idzik KR, Licha T, Lukes V, Rapta P, Frydel J, Schaffer M, Taeuscher E, Beckert R, Dunsch L (2014) Synthesis and optical properties of various thienyl derivatives of pyrene. J Fluoresc 24:153–160

    Article  CAS  PubMed  Google Scholar 

  6. Szuster L, Kazmierska M, Krol I (2004) Fluorescent dyes destined for dyeing high-visibility polyester textile products. Fibres Text East Eur 12:70–75

    CAS  Google Scholar 

  7. Cannestra AF, Pouratian N, Shomer MH, Toga AW (1998) Refractory periods observed by intrinsic signal and fluorescent dye imaging. J Neurophysiol 80:1522–1532

    CAS  PubMed  Google Scholar 

  8. Annenkov VV, Danilovtseva EN, Zelinskiy SN, Basharina TN, Safonova TA, Korneva ES, Likhoshway YV, Grachev MA (2010) Novel fluorescent dyes based on oligopropylamines for the in vivo staining of eukaryotic unicellular algae. Anal Biochem 407:44–51

    Article  CAS  PubMed  Google Scholar 

  9. Obrien JA, Lummis SCR (2007) Diolistics: incorporating fluorescent dyes into biological samples using a gene gun. Trends Biotechnol 25:530–534

    Article  CAS  Google Scholar 

  10. Milanova D, Chambers RD, Bahga SS, Santiago JG (2011) Electrophoretic mobility measurements of fluorescent dyes using on-chip capillary electrophoresis. Electrophoresis 32:3286–3294

    Article  CAS  PubMed  Google Scholar 

  11. Thomas KRJ, Kapoor J, Lee CP, Ho KC (2012) Organic dyes containing pyrenylamine-based cascade donor systems with different aromatic π linkers for dye-sensitized solar cells: optical, electrochemical, and device characteristics. Chem Asian J 7:738–750

    Article  CAS  PubMed  Google Scholar 

  12. Chen KF, Chang CW, Lin JL, Hsu YC, Yeh MCP, Hsu CP, Sun SS (2010) Photophysical studies of dipolar organic dyes that feature a 1,3-cyclohexadiene conjugated linkage: the implication of a twisted intramolecular charge-transfer state on the efficiency of dye-sensitized solar cells. Chem Eur J 16:12873–12882

    Article  CAS  PubMed  Google Scholar 

  13. Al-Eid M, Lim SH, Park KW, Fitzpatrick B, Han CH, Kwak K, Hong J, Cooke G (2014) Facile synthesis of metal-free organic dyes featuring a thienylethynyl spacer for dye sensitized solar cellsq. Dyes Pigment 104:197–203

    Article  CAS  Google Scholar 

  14. Choi H, Baik C, Kim HJ, Kim JJ, Song K, Kang SO, Ko J (2007) Synthesis of novel organic dyes containing coumarin moiety for solar cell. Bull Korean Chem Soc 28:1973–1979

    Article  CAS  Google Scholar 

  15. Wang ZS, Cui Y, Oh YD, Kasada C, Shinpo A, Hara K (2008) Molecular design of coumarin dyes for stable and efficient organic dye-sensitized solar cells. J Phys Chem C 112:17011–17017

    Article  CAS  Google Scholar 

  16. Hardin BE, Snaith HJ, McGehee MD (2012) The renaissance of dye-sensitized solar cells. Nat Photonics 6:162–169

    Article  CAS  Google Scholar 

  17. Chaurasia S, Hung WI, Chou HH, Lin JT (2014) Incorporating a new 2H-[1,2,3]triazolo[4,5-c]pyridine moiety to construct D-A-π-A organic sensitizers for high performance solar cells. Org Lett 16:3052–3057

    Article  CAS  PubMed  Google Scholar 

  18. Auger A, Samuel J, Poncelet O, Raccurt O (2011) A comparative study of non-covalent encapsulation methods for organic dyes into silica nanoparticles. Nanoscale Res Lett 6:328–340

    Article  PubMed Central  PubMed  Google Scholar 

  19. Texier I, Goutayer M, Silva AD, Guyon L, Djaker N (2009) Cyanine-loaded lipid nanoparticles for improved in vivo fluorescence imaging. J Biomed Opt 14:054005. doi:10.1117/1.3213606

    Article  PubMed  Google Scholar 

  20. Huang J, Xu Y, Qian X (2009) A rhodamine-based Hg2+ sensor with high selectivity and sensitivity in aqueous solution: a NS2-containing receptor. J Org Chem 74:2167–2170

    Article  CAS  PubMed  Google Scholar 

  21. Lam KW, Syahida A, Ulhaq Z, Rahman MBA, Lajis NH (2010) Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors. Bioorg Med Chem Lett 20:3755–3759

    Article  CAS  PubMed  Google Scholar 

  22. Li Z, Gu Z, Yin K, Zhang R, Deng Q, Xiang J (2009) Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified D-glucopyranosyl residues and their antiproliferative activities. Eur J Med Chem 44:4716–4720

    Article  CAS  PubMed  Google Scholar 

  23. Li D, Fu H (2006) Synthesis and fungicidal activities of 2,5-Bis[(3-ARYL)-1,2,4-Triazolo[3,4-b]-[1,3,4]Thiadiazole-6-Yl] Pyridines. Heterocycl Commun 12:383–388

    CAS  Google Scholar 

  24. Georgiev NI, Sakr AR, Bojinov VB (2011) Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer. Dyes Pigment 91:332–339

    Article  CAS  Google Scholar 

  25. Garland CW, Nibler JW, Shoemaker DP (2009) Experiments in physical chemistry, 8th edn. The McGraw-Hill Companies, Inc., New York, pp 630–632

    Google Scholar 

  26. Demas JN, Crosby GA (1971) Measurement of photoluminescence quantum yields. Rev J Phys Chem 75:991–1024

    Article  Google Scholar 

  27. Wurth C, Grabolle M, Pauli J, Spieles M, Genger UR (2013) Relative and absolute determination of fluorescence quantum yields of transparent samples. Nat Protoc 8:1535–1550

    Article  PubMed  Google Scholar 

  28. Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer science + business media, LLC, New York, pp 54–55

    Book  Google Scholar 

  29. Brouwer AM (2011) Standards for photoluminescence quantum yield measurements in solution (IUPAC technical report). Pure Appl Chem 83:2213–2228

    Article  CAS  Google Scholar 

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Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2011–0015056).

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  1. Department of Chemistry, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea

    Muhammad Saleem & Ki Hwan Lee

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  1. Muhammad Saleem
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  2. Ki Hwan Lee
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Correspondence to Ki Hwan Lee.

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Saleem, M., Lee, K.H. Synthesis, Characterization and Photophysical Properties of Novel Azole Derivatives. J Fluoresc 25, 217–226 (2015). https://doi.org/10.1007/s10895-015-1505-5

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  • DOI: https://doi.org/10.1007/s10895-015-1505-5

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