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A short survey of the literature is in order to substantiate this point. First, although the fluorescence of n,π*-excited ketones is generally too short-lived and too weak to allow practical exploitation, the steady-state fluorescence of n,π*-excited xanthone has been employed in one case to determine binding constants with cyclodextrins (ref 5). However, the short fluorescence lifetime of xanthone (ca. 0.6-0.8 ns in water, ref 9) precludes dynamic information and, moreover, the solvent dependence is not well understood (Bohne, C., personal communication). Second, compounds with n,π* configuration have been previously employed as fluorescent probes (ref 1), but in the reported examples it is actually not the n,π* state which is fluorescent, but a close-lying π,π* state; the latter becomes the lowest excited state in polar environments ("state switching").
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2O solvent) and, thus, should display a significantly reduced reactivity. Moreover, the hydroxyl groups are located at the rim of the cavity, while DBO is deeply included in the cavity, as suggested by the NMR data.
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