Comparative study on the inclusion behavior between meso-tetrakis(4-N-ethylpyridiniurmyl)porphyrin and β-cyclodextrin derivatives

5,10,15,20-Tetrakis(4-N-ethylpyridiniurmyl)porphyrin (TEPyP) formed 1:1 stoichiometry inclusion complexes with β-cyclodextrin (β-CD) and its derivatives including hydroxypropyl-β-cyclodextrin (HP-β-CD), sulfobutylether-β-cyclodextrin (SBE-β-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 β-CD, HP-β-CD and SBE-β-CD. Association constants as high as K=1.1×104 M−1 in the case of HP-β-CD/TEPyP and 2.0×105 M−1 in the case of SBE-β-CD/TEPyP complexes were determined, whereas a lower value (K=550 M−1) was given in the case of β-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. β-CD and HP-β-CD approached from the primary face of cavities of CDs.