Spectroscopic studies on the inclusion complex of 2-naphthol-6-sulfonate with β-cyclodextrin

被引:33
作者
Abdel-Shafi, Ayman Ayoub [1 ]
机构
[1] Ain Shams Univ, Dept Chem, Fac Sci, Cairo, Egypt
关键词
inclusion complexes; beta-cyclodextrin; naphthol derivatives; fluorescence; Benesi-Hildebrand; H-1; NMR;
D O I
10.1016/j.saa.2006.04.018
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
The photophysical properties of 2-naphthol-6-sulfonate (2-NOH-6-S) in various solvents and in aqueous P-cyclodextrin solution have been investigated. The fluorescence quantum yields in non-aqueous solvents are approximately 0.20 +/- 0.02, while in water the yield is higher. The fluorescence quantum yield in water was found to depend on the pH value of the medium and increases as the pH increase up to a pH value of 4.0 where it comes to be constant. Absorption and fluorescence measurements show 1:1 inclusion of 2-NOH-6-S in the beta-cyclodextrin cavity. The association constant of 2-NOH-6-S-beta-cyclodextrin complex based on fluorescence measurements was calculated using Benesi-Hildbrand relationship and found to be 330 +/- 30 M-1. H-1 NMR studies are used to confirm the inclusion and to provide information on the geometry of 2-NOH-6-S inside the cavity of beta-cyclodextrin. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:732 / 738
页数:7
相关论文
共 62 条
[21]   Effect of pressure on proton transfer rate from a photoacid to a solvent. 3. 2-naphthol and 2-naphthol monosulfonate derivatives in water [J].
Genosar, L ;
Leiderman, P ;
Koifman, N ;
Huppert, D .
JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (10) :1779-1789
[22]   1H-NMR investigation of the binding of 2-methylnaphthalene to α-cyclodextrin in D2O solutions [J].
Hamai, S ;
Ikeda, H ;
Ueno, A .
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1998, 31 (03) :265-273
[23]   Effects of cyclodextrins on the fluorescence of 2-methylnaphth[2,3-d]oxazole in aqueous solution [J].
Hamai, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (08) :1459-1464
[24]   Inclusion complexes of poly-β-cyclodextrin with 2-anilino-6-naphthalenesulfonic acid, 1-chloronaphthalene, and azulene in aqueous solutions [J].
Hamai, S .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1999, 124 (03) :153-158
[25]   EXCITED-STATE PROTON-TRANSFER OF PROTONATED 1-AMINOPYRENE COMPLEXED WITH BETA-CYCLODEXTRIN [J].
HANSEN, JE ;
PINES, E ;
FLEMING, GR .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (17) :6904-6910
[26]   INTERACTION OF CYCLODEXTRIN-CONTAINING POLYMERS WITH FLUORESCENT COMPOUNDS [J].
HARADA, A ;
FURUE, M ;
NOZAKURA, S .
MACROMOLECULES, 1977, 10 (03) :676-681
[27]   ACID-BASE PROPERTIES OF 1-NAPHTHOL - PROTON-INDUCED FLUORESCENCE QUENCHING [J].
HARRIS, CM ;
SELINGER, BK .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (11) :1366-1371
[28]   PROTON-INDUCED FLUORESCENCE QUENCHING OF 2-NAPHTHOL [J].
HARRIS, CM ;
SELINGER, BK .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (08) :891-898
[29]  
HUPPERT D, 1981, ADV CHEM PHYS, V47, P681
[30]   EFFECT OF PRESSURE ON PROTON-TRANSFER RATE IN AQUEOUS-SOLUTIONS - A PICOSECOND STUDY [J].
HUPPERT, DH ;
JAYARAMAN, A ;
MAINES, RG ;
STEYERT, DW ;
RENTZEPIS, PM .
JOURNAL OF CHEMICAL PHYSICS, 1984, 81 (12) :5596-5600