T. Kuwabara et al., Phenolphthalein-modified beta-cyclodextrin as a molecule-responsive colorless-to-color change indicator, J ORG CHEM, 63(24), 1998, pp. 8729-8735
Phenolphthalein-modified beta-CD, 1, was synthesized for the purpose of dev
eloping a new type of guest-responsive color change indicator. The pH titra
tion curve of I depends on its concentration, suggesting that I exists not
only as an self-inclusion form but also as an association form at a concent
ration of 10(-4) M in neutral aqueous solution. At pH 11.0, the association
species dissociates into the monomer one, taking a dianion form in the phe
nolphthalein part. Upon the guest addition at pH 9.70, 1 exhibits the color
change from colorless to purple at its concentration of 5.0 x 10(-6) M due
to the 1:1 host-guest complex formation. The guest-induced absorption chan
ges were used for molecule sensing. The sensing abilities of 1 for various
guests are roughly parallel to the binding constants.