Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence

Keita Hamasaki, Hiroshi Ikeda, Asao Nakamura, Akihiko Ueno, Fujio Toda, Iwao Suzuki, Tetsuo Osa

Research output: Contribution to journalArticle

290 Citations (Scopus)

Abstract

α-, β-, and γ-cyclodextrin derivatives bearing a p-(dimethylamino)benzoyl (DMAB) moiety (DMAB-αCyD, DMAB-βCyD, and DMAB-γCyD, respectively) have been synthesized as fluorescent sensors of molecular recognition. These compounds show dual fluorescence emission arising from normal planar (NP) and twisted intramolecular charge transfer (TICT) exited states, and among them strong TICT emission was observed for DMAB-βCyD. The induced circular dichroism spectra of the derivatives suggest that only DMAB-βCyD among other derivatives binds the DMAB moiety into its own cavity, forming an intramolecular inclusion complex. This conformation was confirmed by the analysis of its 1H-NMR data and was related to its strong TICT emission. The intensity of the TICT emission of DMAB-βCyD decreased markedly with increasing the concentration of cyclic alchols, monoterpenes, or steroids. This observation was explained by the guest-induced location change of the DMAB moiety from inside to outside of the cavity. Since the TICT emission intensity depended on the size, shape, and polarity of the guest molecules, DMAB-βCyD was useful as a fluorescent chemosensor of molecular recognition.

Original languageEnglish
Pages (from-to)5035-5040
Number of pages6
JournalJournal of the American Chemical Society
Volume115
Issue number12
Publication statusPublished - 1993
Externally publishedYes

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Molecular recognition
Cyclodextrins
Charge transfer
Fluorescence
Sensors
Derivatives
Bearings (structural)
Monoterpenes
Dichroism
Conformations
Steroids
Nuclear magnetic resonance
Molecules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence. / Hamasaki, Keita; Ikeda, Hiroshi; Nakamura, Asao; Ueno, Akihiko; Toda, Fujio; Suzuki, Iwao; Osa, Tetsuo.

In: Journal of the American Chemical Society, Vol. 115, No. 12, 1993, p. 5035-5040.

Research output: Contribution to journalArticle

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T1 - Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence

AU - Hamasaki, Keita

AU - Ikeda, Hiroshi

AU - Nakamura, Asao

AU - Ueno, Akihiko

AU - Toda, Fujio

AU - Suzuki, Iwao

AU - Osa, Tetsuo

PY - 1993

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N2 - α-, β-, and γ-cyclodextrin derivatives bearing a p-(dimethylamino)benzoyl (DMAB) moiety (DMAB-αCyD, DMAB-βCyD, and DMAB-γCyD, respectively) have been synthesized as fluorescent sensors of molecular recognition. These compounds show dual fluorescence emission arising from normal planar (NP) and twisted intramolecular charge transfer (TICT) exited states, and among them strong TICT emission was observed for DMAB-βCyD. The induced circular dichroism spectra of the derivatives suggest that only DMAB-βCyD among other derivatives binds the DMAB moiety into its own cavity, forming an intramolecular inclusion complex. This conformation was confirmed by the analysis of its 1H-NMR data and was related to its strong TICT emission. The intensity of the TICT emission of DMAB-βCyD decreased markedly with increasing the concentration of cyclic alchols, monoterpenes, or steroids. This observation was explained by the guest-induced location change of the DMAB moiety from inside to outside of the cavity. Since the TICT emission intensity depended on the size, shape, and polarity of the guest molecules, DMAB-βCyD was useful as a fluorescent chemosensor of molecular recognition.

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