Comparative study on the inclusion behavior between meso-tetrakis(4-N-ethylpyridiniurmyl)porphyrin and beta-cyclodextrin derivatives.
5,10,15,20-Tetrakis(4-N-ethylpyridiniurmyl)porphyrin (TEPyP) formed 1:1 stoichiometry inclusion complexes with beta-cyclodextrin (beta-CD) and its derivatives including hydroxypropyl-beta-cyclodextrin (HP-beta-CD), sulfobutylether-beta-cyclodextrin (SBE-beta-CD) in basic aqueous solution. The supramolecular system was investigated by the methods of fluorescence, UV-vis absorption spectroscopy, nuclear magnetic resonance (NMR) technique. The inclusion ability of cyclodextrins exhibited remarkable difference for beta-CD, HP-beta-CD and SBE-beta-CD. Association constants as high as K=1.1 x 10(4) M(-1) in the case of HP-beta-CD/TEPyP and 2.0 x 10(5) M(-1) in the case of SBE-beta-CD/TEPyP complexes were determined, whereas a lower value (K=550 M(-1)) was given in the case of beta-CD/TEPyP. The results showed that hydrogen bonding and charge attraction play important roles in the processes of host-guest interaction. The interaction mechanism of inclusion processes could be explained by the analysis of NMR spectroscopy. The supramolecular assembly was formed. beta-CD and HP-beta-CD approached from the primary face of cavities of CDs.
Xiliang
Guo
G
School of Chemistry and Chemical Engineering, Institute of Advanced Chemistry, Shanxi University, Taiyuan 030006, China.
Shaomin
Shuang
S
Chuan
Dong
D
Feng
Feng
F
Wong
M S
MS
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002942:Circular Dichroism; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D047392:beta-Cyclodextrins / Q000737:chemistry* / Q000378:metabolism
D011166:Porphyrins; D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C093196:SBE4-beta-cyclodextrin