Abstract:The effect of phenol and aniline derivatives on the lucigenin-H2O2-Co2+ chemiluminescence (CL) at different pH was studied. In NaHCO-Na2CO3 medium, some compounds enhanced the lucigenin CL while others inhibited the lucigenin CL. In NaOH medium, all tested compounds inhibited the lucigenin CL. It was found that the magnitude of enhancement and inhibition by tested compounds was related to their molecular structures, media, and pH. The fluorescence spectra of the system after the CL reaction and the CL spectra of the lucigenin system were studied. The possible mechanisms for CL enhancement and inhibition have been proposed. On the one hand, the competition of phenol and aniline derivatives with lucegenin for H2O2/HO-2 led to the inhibition. On the other hand, the nucleophilic adducts of lucigenin formed by the reactions of some phenol and aniline derivatives with lucegin reacted with lucigenin to give rise to lucigenin radicals, followed by the reactions with the dissolved oxygen to give CL, resulting in the enhancement. The competition of these two routes led to the CL enhancement or inhibition under different conditions.
石明娟,Aung Myint,董永平,崔华*. 苯酚和苯胺类化合物对光泽精化学发光的增强和抑制作用[J]. 光谱学与光谱分析, 2007, 27(10): 1945-1950.
SHI Ming-juan,Aung Myint, DONG Yong-ping,CUI Hua*. The Enhancement and Inhibition of Lucigenin Chemiluminescence by Phenol and Aniline Derivatives. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2007, 27(10): 1945-1950.
[1] Fletcher P, Andrew K N. Luminescence, 2001, 16: 1. [2] Bowie A R, Sanders M G, Worsfold P J. J. Biolumin. Chemilumin., 1996, 11: 61. [3] ZHUANG Hui-sheng, WANG Qiong-e, WU Fang(庄惠生,王琼娥,吴 芳). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2004, 24(8): 927. [4] Liu M L, Li B X, Zhang Z J, et al. Anal. Bioanal. Chem., 2005, 381: 828. [5] Wang Z P, Zhang Z J, Fu Z F, et al. Anal. Bioanal. Chem., 2004, 378: 834. [6] Liang Y D, Song J F, Yang X F. Anal. Chim. Acta, 2004, 510: 21. [7] Du J X, Li Y H, Lu J R. Talanta, 2002, 57: 661. [8] LI Nian-bing, DUAN Jian-ping, CHEN Hong-qing, et al(李念兵,段建平,陈红青,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2004, 24(1): 15. [9] YANG Feng-zhen, ZHANG Chao, WANG Jian-ning, et al(杨凤珍,张 超,王建宁,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2004, 24(2): 145. [10] Gleu K, Petsch W. Angew. Chem., 1935, 48: 57. [11] Totter J R. Photochem. Photobiol., 1964, 3: 231. [12] Maskiewicz R, Sogah D, Bruice T C. J. Am. Chem. Soc., 1979, 101: 5347. [13] Maskiewicz R, Sogah D, Bruice T C. J. Am. Chem. Soc., 1979, 101: 5355. [14] Maeda D, Kashiwabara T, Tokuyama M. Bull. Chem. Soc. Jpn., 1977, 50: 473. [15] Zhang L H, Teshima N, Hasebe T, et al. Talanta, 1999, 50: 677. [16] Parij N, Nagy A M, Fondu P, et al. J. Pharmacol., 1998, 352: 299. [17] Veazey R L, et al. Anal. Chem., 1979, 51: 2092. [18] Papadopoulos K, Triantis T, Yannakopoulou E, et al. Anal. Chim. Acta, 2003, 494: 41. [19] Klinger W, Karge E, Kretzschmar M, et al. Exp. Toxicol. Pathol., 1996, 48: 447. [20] Montano L A, Ingle J D. Anal. Chem., 1979, 51: 919. [21] Montano L A, Ingle J D. Anal. Chem., 1979, 51: 926. [22] Cui H, Meng R, Jiang H Y, et al. Luminescence, 1999, 14: 175. [23] Cui H, Shi M J, Meng R, et al. Photochem. Photobiol., 2004, 79: 233. [24] Legg K D, Hercules D M. J. Am. Chem. Soc., 1969, 91: 1902. [25] TA N. Luminescence Technique in Chemical and Biochemical Analysis. New York: Marcel Dekker, Inc., 1991. [26] Rice-Evans C A, Miller N J, Paganga G. Trends Plant Sci., 1997, 2: 152. [27] Villano D, Fernandez-Pachon M S, Troncoso A M, et al. Anal. Chim. Acta, 2005, 538: 391. [28] Vinson J A, Mandarano M, Hirst M, et al. J. Agric. Food Chem., 2003, 51: 5528. [29] Vinson J A, Jang J H, Dabbagh Y A, et al. J. Agric. Food Chem., 1995, 43: 2798. [30] Sawicki E. Photometric Organic Analysis, Part 1,London: Wiley Interscience, 1970. [31] Eickhoff H, Jung G, Rieker A. Tetrahedron, 2001, 57: 353. [32] Friedman M, Jurgens H S. J. Agric. Food Chem., 2000, 48: 2101. [33] Barton D, Ollis W D. Comprehensive Organic Chemistry: the Synthesis and Reactions of Organic Compounds Vol.1. Oxford:Pergamon Press,1979. [34] Abrash H A, Shih D, Elias W, et al. Int. J. Chem. Kinet., 1989, 21: 465. [35] Wang D G, Gy Orgy I, Hidenbrand K, et al. J. Chem. Soc. Perking Trans., 1994, 2: 45. [36] Lohrie M W K. J. Am. Chem. Soc., 1993, 115: 919. [37] Totter J R. Photochem. Photobiol., 1975, 22: 203. [38] Janzen E G, Pickett J B, Happ J W, et al. J. Org. Chem., 1970, 35: 88.