Abstract:The inclusion interaction of perhydroxycucurbit[6]uril(HOCB6) with methyl orange (MO) was studied by UV spectroscopic and fluorimetric methods. Several effect factors,such as pH values,common organic solvents and surfactants on the fluorescence intensity and the stability of the complex were investigated. The results indicate that the fluorescence intensity of MO was enhanced with a blue shift as host molecules were added,showing that MO was accommodated into the hydrophobic cavities of HOCB6 and an endo-inclusion complex was formed. The hydrophobic interaction between HOCB6 and MO mainly contributed to the formation of 1∶1 type HOCB6-MO. Its complex constant was determined to be 1.41×102 L·mol-1. The comparative study of HOCB6 with other supramolecules,such as cucurbit[6]uril(CB6),p-(N,N-dimethyl-aminomethyl)calix[8]arene and β-cyclodextrin,was also carried out by using MO as a guest probe. The spectra changes showed that cucurbit[6]uril (CB6) can also form 1∶1 type endo-inclusion complex with MO,which is similar to HOCB6,but its complex constant(34.65 L·mol-1) is small. The spectra changes also showed that the endo-inclusion complex with 2∶1 type was formed between β-cyclodextrin and MO,While the exo-inclusion complex was formed between p-(N,N-dimethyl-aminomethyl)calix[8]arene and MO,leading to fluorescence quenching,and their complex constants were determined to be 6.14×106 L2 mol-2 and 1.35×104 L·mol-1,respectively.
李来生,葛小辉,黄志兵,李艳平. 光谱法研究羟基葫芦[6]脲与甲基橙的分子识别作用[J]. 光谱学与光谱分析, 2007, 27(07): 1393-1397.
LI Lai-sheng,GE Xiao-hui,HUANG Zhi-bing,LI Yan-ping. Study on the Molecular Recognition of Perhydroxycucurbit[6]uril with Methyl Orange by Spectroscopic Methods . SPECTROSCOPY AND SPECTRAL ANALYSIS, 2007, 27(07): 1393-1397.
[1] Behrend R,Meyer E,Rusche F. Liebigs Ann. Chem.,1905,339: 1. [2] Freeman W A,Mock W L,Shih N Y. J. Am. Chem. Soc.,1981,103(24): 7367. [3] Day A,Arnold A P,Blanch R J,et al. J. Org. Chem.,2001,66(24): 8094. [4] Zhao J Z,Kim H J,Oh J,et al. Angew. Chem. Int. Ed. Engl.,2001,40(22): 4233. [5] Islobe H,Sato S,Nakamura E. Org. Let.,2002,4(8): 1287. [6] Jon S Y,Selvapalam N,Oh D H,et al. J. Am. Chem. Soc.,2003,125(34): 10186. [7] Jun S I,Lee J W,Sakamoto S,et al. Tetrahedron Lett.,2000,41(4): 471. [8] Buschmann H J,Jansen K,Schollmeyer E. Inorg. Chem. Commun.,2003,6: 531. [9] Wanger B D,Stojanovic N,Day A I,et al. J. Phys. Chem. B,2003,107: 10741. [10] Gutsche C D,Nam K C. J. Am. Chem. Soc.,1988,110(18): 6153. [11] HAN Bao-hang,LIU Yu(韩宝航,刘 育). Chinese Journal of Organic Chemistry(有机化学),2003,23(2): 139. [12] Kerry K K,Daniel A S,Christine T L,et al. Journal of Colloid and Interface Science,1998,203: 157. [13] LIU Xiu-ping,ZHANG Guo-mei,YANG Yu,et al(刘秀萍,张国梅,杨 郁,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析),2004,24(3): 323. [14] LU Ping,LIU Bin,WU Feng,et al(路 平,刘 彬,吴 峰,等). Chinese Journal of Applied Chemistry(应用化学),2003,20(2): 108. [15] HUANG Zhi-bing,LI Lai-sheng,WANG Yu-xiao,et al(黄志兵,李来生,王宇晓,等). Spectroscopy and Spectral Analysis(光谱学与光谱分析),2005,25(4): 591.