Association of 1: 1 inclusion complexes of cyclodextrins into homo- and heterodimers: A spectroscopic study using a TICT-forming fluorescent probe as a guest compound

Asao Nakamura, Shiro Sato, Keita Hamasaki, Akihiko Ueno, Fujio Toda

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58 Citations (Scopus)

Abstract

A 1:1 complex of 6-O-α-D-glucosyl-β-cyclodextrin (G1-β-CD) with 4-(dimethylamino)benzonitrile (DMABN) associates with itself in aqueous solutions at high concentrations into a 2:2 complex (homodimer). The 1:1 complex of G1-β-CD with DMABN also makes a heterodimer (1:1:2 complex) by the association with a 1:1 inclusion complex of another guest molecule such as 1-pentanol, benzene, anisole, and benzonitrile. The association of the complex is accompanied by a drastic change in the fluorescence spectrum of DMABN. The measurement of the fluorescence intensity as a function of the concentration of G1-β-CD gave the equilibrium constants for the association. The equilibrium constants were greatly dependent on the temperature, and the values for both ΔH and ΔS were largely negative. The fluorescence spectra of DMABN in the cavity of the dimers changed with exchanging the second guest compound, which implies that the second guest molecule plays the role of a polar solvent in the nonpolar environment in the cavity. The formation of homo- and heterodimers of the 1:1 inclusion complex also takes place in the solutions containing other cyclodextrins and DMABN.

Original languageEnglish
Pages (from-to)10952-10959
Number of pages8
JournalJournal of Physical Chemistry
Volume99
Issue number27
Publication statusPublished - 1995
Externally publishedYes

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Cyclodextrins
Fluorescent Dyes
Fluorescence
Equilibrium constants
Association reactions
inclusions
fluorescence
probes
anisole
cavities
Molecules
exchanging
Dimers
molecules
Benzene
benzene
dimers
aqueous solutions
benzonitrile
Temperature

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

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title = "Association of 1: 1 inclusion complexes of cyclodextrins into homo- and heterodimers: A spectroscopic study using a TICT-forming fluorescent probe as a guest compound",
abstract = "A 1:1 complex of 6-O-α-D-glucosyl-β-cyclodextrin (G1-β-CD) with 4-(dimethylamino)benzonitrile (DMABN) associates with itself in aqueous solutions at high concentrations into a 2:2 complex (homodimer). The 1:1 complex of G1-β-CD with DMABN also makes a heterodimer (1:1:2 complex) by the association with a 1:1 inclusion complex of another guest molecule such as 1-pentanol, benzene, anisole, and benzonitrile. The association of the complex is accompanied by a drastic change in the fluorescence spectrum of DMABN. The measurement of the fluorescence intensity as a function of the concentration of G1-β-CD gave the equilibrium constants for the association. The equilibrium constants were greatly dependent on the temperature, and the values for both ΔH and ΔS were largely negative. The fluorescence spectra of DMABN in the cavity of the dimers changed with exchanging the second guest compound, which implies that the second guest molecule plays the role of a polar solvent in the nonpolar environment in the cavity. The formation of homo- and heterodimers of the 1:1 inclusion complex also takes place in the solutions containing other cyclodextrins and DMABN.",
author = "Asao Nakamura and Shiro Sato and Keita Hamasaki and Akihiko Ueno and Fujio Toda",
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journal = "Journal of Physical Chemistry",
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T2 - 1 inclusion complexes of cyclodextrins into homo- and heterodimers: A spectroscopic study using a TICT-forming fluorescent probe as a guest compound

AU - Nakamura, Asao

AU - Sato, Shiro

AU - Hamasaki, Keita

AU - Ueno, Akihiko

AU - Toda, Fujio

PY - 1995

Y1 - 1995

N2 - A 1:1 complex of 6-O-α-D-glucosyl-β-cyclodextrin (G1-β-CD) with 4-(dimethylamino)benzonitrile (DMABN) associates with itself in aqueous solutions at high concentrations into a 2:2 complex (homodimer). The 1:1 complex of G1-β-CD with DMABN also makes a heterodimer (1:1:2 complex) by the association with a 1:1 inclusion complex of another guest molecule such as 1-pentanol, benzene, anisole, and benzonitrile. The association of the complex is accompanied by a drastic change in the fluorescence spectrum of DMABN. The measurement of the fluorescence intensity as a function of the concentration of G1-β-CD gave the equilibrium constants for the association. The equilibrium constants were greatly dependent on the temperature, and the values for both ΔH and ΔS were largely negative. The fluorescence spectra of DMABN in the cavity of the dimers changed with exchanging the second guest compound, which implies that the second guest molecule plays the role of a polar solvent in the nonpolar environment in the cavity. The formation of homo- and heterodimers of the 1:1 inclusion complex also takes place in the solutions containing other cyclodextrins and DMABN.

AB - A 1:1 complex of 6-O-α-D-glucosyl-β-cyclodextrin (G1-β-CD) with 4-(dimethylamino)benzonitrile (DMABN) associates with itself in aqueous solutions at high concentrations into a 2:2 complex (homodimer). The 1:1 complex of G1-β-CD with DMABN also makes a heterodimer (1:1:2 complex) by the association with a 1:1 inclusion complex of another guest molecule such as 1-pentanol, benzene, anisole, and benzonitrile. The association of the complex is accompanied by a drastic change in the fluorescence spectrum of DMABN. The measurement of the fluorescence intensity as a function of the concentration of G1-β-CD gave the equilibrium constants for the association. The equilibrium constants were greatly dependent on the temperature, and the values for both ΔH and ΔS were largely negative. The fluorescence spectra of DMABN in the cavity of the dimers changed with exchanging the second guest compound, which implies that the second guest molecule plays the role of a polar solvent in the nonpolar environment in the cavity. The formation of homo- and heterodimers of the 1:1 inclusion complex also takes place in the solutions containing other cyclodextrins and DMABN.

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