Fluorescence techniques were employed to study the inclusion complexes of 2-methylnaphthoate (MN) with 2-hydroxypropyl-α-cyclodextrin (αHPCD), 2-hydroxypropyl-β-cyclodextrin (βHPCD), and 2-hydroxypropyl-γ-cyclodextrin (γHPCD). Emission spectra of MN show two vibronic bands whose intensity ratio <i>R</i> is very sensitive to the polarity of the medium. The stoichiometry and formation constants of these complexes were investigated by obtaining <i>R</i> as a function of the cyclodextrin (CD) concentration. Results showed identical stoichiometry (1/1) for the three MN/αHPCD, MN/β-HPCD, and MN/γHPCD complexes. Formation constants at 25°C were 780 ± 15, 2700 ± 130, and 165 ± 10 M<sup>-1</sup>, respectively. ΔH0 and ΔS<sup>0</sup> were obtained from linear van't Hoff plots. Results reveal that the complexation of MN with αHPCD is enthalpy driven. With βHPCD, both the entropy and enthalpy terms favor the process, whereas the formation of the complex with γHPCD is entropically governed. The extrapolation of <i>R</i> at infinite CD concentration allows us to estimate the effective dielectric constants of the inner CD cavities, which are around 50, but which differ from their counterparts, the naturally occurring α-, β-, and γ-CDs. Fluorescence anisotropy, quencher lifetimes, and average lifetimes can also give additional information about the structure and driving forces accompanying the formation of such complexes.

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