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

doi:10.1021/jo980613i

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

Research output: Contribution to journal › Article › peer-review

59 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 language	English
Pages (from-to)	8729-8735
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	63
Issue number	24
DOIs	https://doi.org/10.1021/jo980613i
Publication status	Published - 1998 Nov 27
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo980613i

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title = "Phenolphthalein-modified β-cyclodextrin as a molecule-responsive colorless-to-color change indicator",

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.",

author = "Tetsuo Kuwabara and Makoto Takamura and Akiko Matsushita and Hiroshi Ikeda and Asao Nakamura and Akihiko Ueno and Fujio Toda",

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T1 - Phenolphthalein-modified β-cyclodextrin as a molecule-responsive colorless-to-color change indicator

AU - Kuwabara, Tetsuo

AU - Takamura, Makoto

AU - Matsushita, Akiko

AU - Ikeda, Hiroshi

AU - Nakamura, Asao

AU - Ueno, Akihiko

AU - Toda, Fujio

PY - 1998/11/27

Y1 - 1998/11/27

N2 - 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.

AB - 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.

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

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