A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin

Yoshimi Sueishi, Ayari Itoh, Naoya Inazumi, Yoshihiro Osawa, Tadashi Hanaya

Research output: Contribution to journalArticle

Abstract

The inclusion complexations of paracyclophane (CP44) and β-cyclodextrin (β-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. β-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van’t Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on 1H- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the β-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of β-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and β-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and β-CD plays an important role in quantum yield enhancement upon inclusion.

Original languageEnglish
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume91
Issue number1-2
DOIs
Publication statusPublished - Jun 1 2018

Fingerprint

cyclodextrins
Sulfonic Acids
sulfonic acid
Cyclodextrins
Complexation
inclusions
Fluorescence
fluorescence
naphthalene
polarity
enthalpy
tetraaza(6.1.6.1)paracyclophane
Thermodynamics
thermodynamics
Molecular recognition
cavities
augmentation
Quantum yield
Temperature
Enthalpy

Keywords

  • Anilinonaphthalene sulfonic acid
  • Cyclodextrin
  • Cyclophane
  • Inclusion complexation
  • Quantum yield of inclusion complex

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

Cite this

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title = "A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin",
abstract = "The inclusion complexations of paracyclophane (CP44) and β-cyclodextrin (β-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. β-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van’t Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on 1H- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the β-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of β-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and β-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and β-CD plays an important role in quantum yield enhancement upon inclusion.",
keywords = "Anilinonaphthalene sulfonic acid, Cyclodextrin, Cyclophane, Inclusion complexation, Quantum yield of inclusion complex",
author = "Yoshimi Sueishi and Ayari Itoh and Naoya Inazumi and Yoshihiro Osawa and Tadashi Hanaya",
year = "2018",
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TY - JOUR

T1 - A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin

AU - Sueishi, Yoshimi

AU - Itoh, Ayari

AU - Inazumi, Naoya

AU - Osawa, Yoshihiro

AU - Hanaya, Tadashi

PY - 2018/6/1

Y1 - 2018/6/1

N2 - The inclusion complexations of paracyclophane (CP44) and β-cyclodextrin (β-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. β-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van’t Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on 1H- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the β-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of β-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and β-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and β-CD plays an important role in quantum yield enhancement upon inclusion.

AB - The inclusion complexations of paracyclophane (CP44) and β-cyclodextrin (β-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. β-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van’t Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on 1H- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the β-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of β-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and β-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and β-CD plays an important role in quantum yield enhancement upon inclusion.

KW - Anilinonaphthalene sulfonic acid

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KW - Inclusion complexation

KW - Quantum yield of inclusion complex

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