Synthesis and Fluorescence Properties of Pyrazole Oxadiazole Derivatives

Abstract:

Article Preview

In order to explore high strength organic electrotransporting electroluminescent (EL) materials, twelve new pyrazole oxadiazole compounds containing the benzothiazole or benzene group in the 1 position of pyrazole, the aromatic group in the 3 position of pyrazole and the formacyl group in the 4 position of pyrazole were designed and synthesized. A new method of synthesizing 1,3,4-oxadiazole compound was described. Their structures were characterized by IR, MS, 1H NMR spectra and elemental analysis. The fluorescence properties were measured by fluorometry. The results showed that the target compounds had good fluorescence and λem ranged from 410nm to 450 nm and fluorescence quantum yields up to 0.69.

Info:

Periodical:

Advanced Materials Research (Volumes 455-456)

Edited by:

Khine Soe Thaung

Pages:

565-574

Citation:

D. F. Li et al., "Synthesis and Fluorescence Properties of Pyrazole Oxadiazole Derivatives", Advanced Materials Research, Vols. 455-456, pp. 565-574, 2012

Online since:

January 2012

Export:

Price:

$38.00

[1] Y. Kaminorz, C. Xu, B. Schulz, B. Stiller, J. Reiche, W. Regenstein, L. Brehmer, Ordered films of a new substituted diphenyl-1, 3, 4-oxadiazole for application in light emitting devices. Synth. Met. 127 (2002) 217–220.

DOI: https://doi.org/10.1016/s0379-6779(01)00626-9

[2] J.H. Kin, J.H. Park, H. Lee, Highly efficient novel poly(p-phenylenevinylene) derivative with 1, 3, 4-oxadiazole pendant on a vinylene unit. Chem. Mater. 15 (2003) 3414–3416.

DOI: https://doi.org/10.1021/cm034134y

[3] D. Udayakumar, A.V. Adhikari, Synthesis and characterization of novel conjugated copolymers containing 3, 4-dialkoxythiophene and 1, 3, 4-oxadiazole units. Eur. Polym. J. 43 (2007) 3488–3499.

DOI: https://doi.org/10.1016/j.eurpolymj.2007.04.030

[4] C.K. Kwak, C.H. Lee, T.S. Lee, A new series of 2, 5-bis(4-methylphenyl)-1, 3, 4-oxadiazole derivatives: their synthesis and fluorescence properties for anion sensors. Tetrahedron Lett. 48 (2007) 7788–7792.

DOI: https://doi.org/10.1016/j.tetlet.2007.09.008

[5] P.K. Hegde, A.V. Adhikari, M. G. Manjunatha, P. Poornesh, G. Umesh, Third-order nonlinear optical susceptibilities of new copolymers containing alternate 3, 4-dialkoxythiophene and (1, 3, 4-oxadiazolyl) pyridine moieties. Opt. Mater. 31 (2009).

DOI: https://doi.org/10.1016/j.optmat.2008.11.015

[6] T.H. Lee, K. M. Lai, L.M. Leung, Hole-limiting conductive vinyl copolymers for AlQ3-based OLED applications. Polymer 50 (2009) 4602–4611.

DOI: https://doi.org/10.1016/j.polymer.2009.07.034

[7] M. Abdel-Aziz, G.E.D.A. Abuo-Rahma, A.A. Hassan, Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur. J. Med. Chem. 44 (2009) 3480–3487.

DOI: https://doi.org/10.1002/chin.200948129

[8] F. Silva, F. Marques, I.C. Santos, A. Paulo, A.S. Rodriguesb, J. Rueffb, I. Santos, Synthesis, characterization and cytotoxic activity of gallium (III) complexes anchored by tridentate pyrazole-based ligands. J. Inorg. Biochem. 104 (2010) 523–532.

DOI: https://doi.org/10.1016/j.jinorgbio.2010.01.003

[9] S. Sidique, S.A. Shiryaev, B.I. Ratnikov, A. Herath, Y. Su, A.Y. Stronginb, N.D.P. Cosford, Structure-activity relationship and improved hydrolytic stability of pyrazole derivatives that are allosteric inhibitors of West Nile Virus NS2B-NS3 proteinase. Bioorg. Med. Chem. Lett. 19 (2009).

DOI: https://doi.org/10.1016/j.bmcl.2009.07.150

[10] S. Pu, T. Yang, J. Xu, B. Chen, Syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit. Tetrahedron Lett. 47 (2006) 6473–6477.

DOI: https://doi.org/10.1016/j.tetlet.2006.06.073

[11] S. Gupta, B.K. Paul, A.K. Barik, T.N. Mandal, S. Roy, N. Guchhait, R.J. Butcher, S.K. Kar, Modulation of fluorescence emission of 1-(2-pyridyl)pyrazole derived Schiff base ligands by exploiting their metal ion sensitive binding modes. Polyhedron 28 (2009).

DOI: https://doi.org/10.1016/j.poly.2009.07.053

[12] X. Wang, W. Li, X.H. Zhang, D.Z. Liu, X.Q. Zhou, A study on the synthesis and photophysical performances of some pyrazole and triazole fluorescent brightening agents. Dyes Pigments 64 (2005) 141–146.

DOI: https://doi.org/10.1016/j.dyepig.2004.04.010

[13] H. Fu, X. Gao, G. Zhong, Z. Zhong, F. Xiao, B. Shao, Synthesis and electroluminescence properties of benzothiazole derivatives. J. Lumin. 129 (2009) 1207–1214.

DOI: https://doi.org/10.1016/j.jlumin.2009.06.004

[14] E. Belgodere, R. Bossio, S. Chimichi, V. Parrini, R. Pepino, Synthesis and fluorescence of some thiazole and benzothiazole derivatives. Dyes Pigments 4 (1983) 59–71.

DOI: https://doi.org/10.1002/chin.198323337

[15] K.D. Belfield, M.V. Bondar, O.V. Przhonskab, K.J. Schafera, Photophysical characterization of 2, 9-bis (7-benzothiazole-9, 9'-didecylfluoren-2-yl) perylene diimide: a new standard for steady-state fluorescence anisotropy. J. Photochem. Photobiol. A: Chem. 151 (2002).

DOI: https://doi.org/10.1016/s1010-6030(02)00176-4

[16] S.K. Saha, P. Purkayastha, A.B. Das, Photophysical characterization and effect of pH on the twisted intramolecular charge transfer fluorescence of trans-2-[4-(dimethylamino)styryl] benzothiazole. J. Photochem. Photobiol. A: Chem. 195 (2008).

DOI: https://doi.org/10.1016/j.jphotochem.2007.11.004

[17] D.F. Li, G.J. Jiang, J.S. Li. Synthesis of 1-(2-benzothiazolyl)-3-phenyl pyrazoline and its derivatives. Chem. J. Chin. U. 11 (1990) 205-207.

[18] L.V. Chepeleva, A.Y. Matsakov, Z.A. Kondratyuk, F.G. Yaremenko, A.O. Doroshenko, Pyrazolyc 3-hydroxychromones. J. Photochem. Photobiol. A: Chem. 209 (2010) 163–173.

[19] S.K. Dogra, Spectral characteristics of 2-(3', 5'-diaminophenyl) benzothiazole: effects of solvents and acid-base concentrations. J. Photochem. Photobiol. A: Chem. 172 (2005) 185–195.

DOI: https://doi.org/10.1016/j.jphotochem.2004.12.008