Phenolphthalein-modified beta-cyclodextrin as a molecule-responsive colorless-to-color change indicator

Citation
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
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
63
Issue
24
Year of publication
1998
Pages
8729 - 8735
Database
ISI
SICI code
0022-3263(19981127)63:24<8729:PBAAMC>2.0.ZU;2-V
Abstract
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.