Novel β-cyclodextrin-[60]fullerene conjugates based on Huisgen [2+3] cycloaddition: synthesis and dyes complexation properties

By using β-cyclodextrin aromatic aldehyde derivatives 5 and 6 as starting materials, the novel β-cyclodextrin-[60]fullerene conjugate 7 and bis-β-cyclodextrin-[60]fullerene conjugate 8 were designed and conveniently synthesized via the Huisgen [2+3] cycloaddition for the first time. The UV–Vis complexation experiments, fluorescence titration spectra and complexation ESI–MS spectrum suggested that they possessed excellent binding abilities for dyes with 1:1 host–guest complexes. The highest association constant of compound 8 for Orange I was as high as 6.97 × 105.