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

Tetsuo Kuwabara, Makoto Takamura, Akiko Matsushita, Hiroshi Ikeda, Asao Nakamura, Akihiko Ueno, Fujio Toda

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54 Citations (Scopus)

Abstract

Phenolphthalein-modified β-CD, 1, was synthesized for the purpose of developing a new type of guest-responsive color change indicator. The pH titration curve of 1 depends on its concentration, suggesting that 1 exists not only as an self-inclusion form but also as an association form at a concentration 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 phenolphthalein 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 changes were used for molecule sensing. The sensing abilities of 1 for various guests are roughly parallel to the binding constants.

Original languageEnglish
Pages (from-to)8729-8735
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number24
DOIs
Publication statusPublished - 1998 Nov 27
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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