Spectrophotometric study of fluorescence sensing and selective binding of biochemical substrates by 2,2'-bridged bis(β-cyclodextrin) and its water-soluble fullerene conjugate

A bis(β-cyclodextrin)−fullerene conjugate (3) linked at the secondary hydroxyl side was prepared in a good yield from its precursor N,N‘-bis(2-(2-aminoethylamino)ethyl)malonamide-bridged bis(β-cyclodextrin) (2). Spectrophotomeric studies on the conformation and the inclusion complexation behavior of 3 with a variety of organic and biochemical substrates by means of UV−vis, FT-IR, NMR, fluorescence, and circular dichroism spectroscopy showed that the bis(β-cyclodextrin)−fullerene conjugate displayed an intramolecular capsule-type conformation in aqueous solution. Because of the multiple binding of bis(β-cyclodextrin) with substrates, 2 can act as an efficient fluorescence sensor for biochemical substrates, while its fullerene conjugate 3 displays a capability of cleaving DNA under visible-light irradiation.