AAC  >> Vol. 4 No. 3 (August 2014)

    吩嗪-5,10-二氮氧化物的合成及光谱性质的研究
    Determination Fluorescence Emission Spectra of Phenazine 5,10-Dioxide Using Multi-Peaks Gaussian Fitting Method in Different Solvent

  • 全文下载: PDF(1365KB) HTML    PP.34-40   DOI: 10.12677/AAC.2014.43006  
  • 下载量: 1,544  浏览量: 8,120  

作者:  

刘 琼,赵明桥:广东产品质量监督检验研究院,顺德;
徐常威,张建华:广州大学化学化工学院,广州

关键词:
吩嗪-510-二氮氧化物荧光光谱高斯多峰拟合单体二聚体Phenazine 510-DioxideFluorescence Spectrum Multi-Peaks Gaussian Fitting Dimer Overlap Peaks

摘要:

在醋酸溶液中用过氧化氢氧化吩嗪合成吩嗪-5,10-二氮氧化物。测量了不同溶剂和浓度条件下吩嗪-5,10-二氮氧化物的荧光发射光谱。其特征是吩嗪-5,10-二氮氧化物二聚体(520~545 nm)发射峰以肩峰方式与单体(500~515 nm)主发射峰叠合在一起。通过高斯多峰拟合实现了单体与二聚体荧光发射光谱叠合峰的分峰拟合计算,得到吩嗪-5,10-二氮氧化物单体与二聚体最大发射峰波长,峰面积等光谱参数,进而求得二聚体与单体相对积分发射强度(I2/I1)与浓度、溶剂的关系。当溶液浓度较低时二聚体/单体相对积分发射强度呈线性增大,随着溶液浓度的增加,单体与二聚体最大发射峰发生显著红移。在四氢呋喃、乙酸乙酯、乙腈、乙醇溶液中二聚体/单体的积分相对发射强度I2/I1随浓度的减少而减小,但在苯、甲苯、冰乙酸溶液中随着溶液浓度的降低I2/I1反而增大。

Phenazine 5,10-dioxide has been synthesized by a reaction of phenazine with hydrogen peroxide (H2O2) in acetic acid (HAc) solution. And its fluorescence emission spectra has been determined in different solvent by overlap peaks of a principal peak with a wavelength (λ) at 520 - 545 nm and a shoulder peak with λ at 500 - 515 nm, which are respectively assigned to dimer and monomer emission peaks. The maximum wavelength, peak area, and other spectral parameters for phenazine 5,10-dioxide dimer and monomer were obtained from the analysis of overlap peaks by a mul-ti-peaks Gaussian fitting method, then the value of relative integral emission intensity for dimer and monomer (I2/I1) in different solvents with various concentration can be obtained. When the concentration of phenazine 5,10-dioxide is low, the value of I2/I1 grows linearly with the concen-tration increase, and the maximum emission peaks of the monomer and dimer redly shift signifi-cantly. When the concentration of phenazine 5,10-dioxide is high, the value of I2/I1 grows with the concentration increase in tetrahydrofuran (THF), ethyl acetate, acetonitrile and ethanol, however it decreases with the concentration increase in benzene, toluene and acetic acid (HAc).

文章引用:
刘琼, 赵明桥, 徐常威, 张建华. 吩嗪-5,10-二氮氧化物的合成及光谱性质的研究[J]. 分析化学进展, 2014, 4(3): 34-40. http://dx.doi.org/10.12677/AAC.2014.43006

参考文献

[1] González, M., Cerecetto, H. and Monge, A. (2007) Quinoxaline 1,4-dioxide and phenazine 5,10-dioxide. Chemistry and biology. Topics in Heterocyclic Chemistry, 11, 179-211.
[2] Surpin, M., Zou, Y.F., Xiong, C.Y., et al. (2010) Iodine scanning of a phenazine inhibitor of vacuolar sorting. Bioorganic & Medicinal Chemistry Letters, 20, 1496-1499.
[3] Cerecetto, H., González, M., Lavaggi, M.L., et al. (2005) Phenazine 5,10-dioxide derivatives as hy-poxic selective cytotoxins. Journal of Medical Chemistry, 48, 21-23.
[4] Lavaggi, M.L., Nieves, M., Cabrera, M., et al. (2010) Structural modifications on the phenazine N,N’-dioxide-scaffold looking for new selective hypoxic cytotoxins. European Journal of Medicinal Chemistry, 45, 5362-5369.
[5] Nagai, K. and Hecht, S.M. (1991) Site-specific DNA cleavage by antisense oligonucleotides covalently linked to phenazine di-N-oxide. The Journal of Biological Chemistry, 266, 23994-24002.
[6] Kawata, H., Niizuma, S. and Kokubun, H. (1978) Studies on the photoreaction of heterocyclic N-dioxides: Photochromism of phenazine N-dioxides in organicsolvents. Journal of Photochemistry, 9, 463-471.
[7] Kräßig, R., Bergmann, D., Fliegen, N., et al. (1970) Polarisation der Elektronenbanden von Aromaten 8. Mitteilung: Phenazin, Phenazin-N-oxid, Phenazin-N,N'-dioxid. Berichte der Bunsengesellschaft für physikalische Chemie, 74, 617-623.
[8] Pachón, O.G., Azqueta, A., Lavaggi, M.L., et al. (2008) Antitumoral effect of phenazine N5,N10-dioxide derivatives on Caco-2 cells. Chemical Research in Toxicology, 21, 1578-1585.
[9] Lavaggi, M.L., Aguirre, G., Boiani, L., et al. (2008) Pyrimido[1,2-a]quinoxaline 6-oxide and phenazine 5,10-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. European Journal of Medicinal Chemistry, 43, 1737-1741.
[10] Li, X.G., Zhang, J.H., Liu, Z.Q., et al. (2011) Determination of critical micelle concentration of binary surfactant mixtures using UV-vis spectrophotometry and Gaussian fitting method. Global Journal of Physical Chemistry, 2, 34-38.
[11] Zhang, J.H., Kong, K.Q., He, Z.L., et al. (2007) Determination of critical micelle concentration of alkyl polyglucoside (APG) nonionic surfactant aqueous system by multi-peaks Gaussian fitting of visible absorption spectra line shape. Guang Pu Xue Yu Guang Pu Fen Xi, 27, 1412-1415.
[12] Feng, W.S., Fang, Y., Xu, J.X., et al. (2008) Application of Gaussian multi-peak fitting to radial distribution function. Acta Physico-Chimica Sinica, 24, 497-501.
[13] Babić, S., Horvat, A.J.M., Pavlović, D.M., et al. (2007) Determination of pKa values of active pharma-ceutical ingredients. TrAC Trends in Analytical Chemistry, 26, 1043-1061.
[14] Ross, S.C. and Tsukiyama, K. (2011) Born-oppenheimer breakdown and non-adiabatic lifetimes of rovibrational levels of D2 lying near the n=2 dissociation limit: Experiment and theory. Journal of Molecular Spectroscopy, 265, 15-25.
[15] Smith, D.F. (1959) The overlapping hydrogen fluoride monomer-dimer spectra. Journal of Molecular Spectroscopy, 3, 473-485.
[16] Kecel, S., Ozel, A.E., Akyuz, S., et al. (2010) Conformational analysis and vibrational spectroscopic investigation of L-alanyl-L-glutamine dipeptide. Spectroscopy, 24, 219-232.
[17] Nansathit, A., Apipattarakul, S., Phaosiri, C., et al. (2009) Synthesis, isolation of phenazine derivatives and their antimicrobial activities. Walailak Journal of Science and Technology, 6, 79-91.
[18] Namba, Y. (2010) An X-ray investigation of the single crystal of phenazine 5,10 dioxide. Memoirs of the Osaka University of the Liberal Arts and Education. B, Natural Science, 11, 45-58.
[19] Tafulo, P.A.R., Queirós, R.B. and González-Aguilar, G. (2009) On the “concentration-driven” methylene blue dimerization. Spectrochim. Acta A., 73, 295-300.
[20] Arbeloa, F.L., Liebana, Y.R., Fernández, E.C., et al. (1989) Self-association of the molecular forms of Rhodamine 19. Solvent effect. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 45, 1201-1206.
[21] Lakowicz, J.R. (2006) Principles of fluorescence spectroscopy. 3rd Edition, Springer, New York, 205-208.
[22] Albani, J.R. (2007) Principles and applications of fluorescence spectroscopy. Blackwell, London, 115-123.
[23] Valeur, B. (2002) Molecular fluorescence principles and applications. Wiley-VCH, Weinhelm, 48.