Design on head-to-tail directly linked homogeneous and heterogeneous cyclodextrin dimers and their evaluation of hydrophobic cavity

Covalent directly head-to-tail linked homogeneous and heterogeneous cyclodextrin (CD) dimers were synthesized, and that the reaction of 6-tosylated α-, β-, or γ-CD with a β-CD mono-oxyanion linked the second CD to the secondary hydroxyl side of β-CD was demonstrated. Moreover, deprotonation of α- and γ-CD using NaOH gave corresponding mono-oxyanions, which reacted with the 6-tosylated CDs to produce the CD dimers. The binding of the dimers to sodium 6-(4-tert-butylaniline)-2-naphthalenesulfonate (BNS) was investigated. The binding constant of the 6β-2β-CD dimer with BNS was estimated as 3.2 × 106 M−1, about 102 times larger than that of β-CD monomer.