Investigations of the supramolecular host properties of a fluorescent bistren cage compound
The host properties of a bistren cage compound, previously reported to be an efficient anion sensor, are shown to include encapsulation of small aromatic guest molecules. It is also shown that the intrinsic fluorescence of this cage compound, arising from the anthracenyl moiety in its structure, is sensitive to the encapsulation of aromatic guests in aqueous solution and can be used to measure the binding constants for any such guest. This makes this bistren cage a rare example of a fluorescent host for aromatic guests, and suggests potential applications of this compound as a versatile fluorescent sensor for a variety of guests of interest. The binding of a number of benzene derivatives was studied; these were all found to form 1:2 host–guest inclusion complexes with a wide range in total binding constants (K1K2), from 6.4 × 103 to 3.5 × 107 (mol/L)–2, indicating a significant degree of selectivity for different benzene derivatives. The binding strength was found to depend on both the guest polarity and aqueous solubility.