Spectrofluorometric titrations have been performed to determine the stability constants of inclusion complexation for mono[6- (diethylenetriamino)-6-deoxy]-β-cyclodextrin (1), mono[6- (triethylenetetraamino)-6-deoxy]-β-cyclodextrin (2) and their copper (II) complexes with a series of naphthalene derivatives in phosphate buffer solution (pH7.2, 0.1mol.dm^-^3) at 25℃. The complex abilities of chemically modified cyclodextrins (1-4) were compared with that of native β-cyclodextrin. The supramolecular system stoichiometry is 1: 1 for the inclusion complexation of all naphthalene derivatives with four chemically modified β -cyclodextrins (1-4). The selective binding abilities of host compounds with model substrates are discussed from the viewpoint of size/shape-fitting, geometry compensation and multiple recognition. The results obtained indicate that several noncovalent weak forces, including hydrophobic, van der Waals, electrostatic and hydrogen bonding interactions, cooperatively contribute to the formation of supramolecular complexes. The structural matching between host and guest plays a crucial role in selectively binding substrates to form supramolecular complexes.

Key words: SUPERMOLECULAR STRUCTURE, OLECULAR RECOGNITION, CYCLODEXTRIN, COPPER COMPLEX, NAPHTHALENE, INCLUSION COMPLEXATIONS