The enhancement of fluorescence quantum yields of anilino naphthalene sulfonic acids by inclusion of various cyclodextrins and cucurbit[7]uril

Yoshimi Sueishi, Tomonori Fujita, Shinichiro Nakatani, Naoya Inazumi, Yoshihiro Osawa

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The association constants (K) for the inclusion complexation of four kinds of cyclodextrins (CDs (β- And γ-), 2,6-di-O-methylated β- CD, and 2,3,6-tri-O-methylated β- CD) and cucurbit[7]uril (CB[7]) with 1,8- And 2,6- Anilinonaphthalene sulfonic acids (ANSs) were determined from fluorescence spectra enhanced by inclusion. Various CDs and CB[7] form stable 1:1 inclusion complexes with 1,8- And 2,6-ANSs: K = 80-11700 M-1for 2,6-ANS and 50-195 M-1for 1,8-ANS. The high stability of the inclusion complexes of 2,6-ANS with CB[7] and 2,6-di-O-methylated b-CD is shown. Further, we determined the fluorescence quantum yields (φvalues) for the inclusion complexes of ANSs by using a fluorescence spectrophotometer equipped with a half-moon unit. Theφvalues of 1,8- And 2,6-ANSs were largely enhanced by the inclusion of methylated β-CDs and did not correlate with the degree of stability (K) of the inclusion complexes. We characterized the structures of the inclusion complexes by 2D ROESY-NMR measurements. In addition, the microenvironmental polarity inside the hydrophobic CD and CB[7] cavities was evaluated using the fluorescence probe 2,6-ANS. Based on the emission mechanism and the aspect of inclusion in a hydrophobic cavity, we have suggested that the microenvironmental polarity and viscosity for the excited state of ANS plays an important role for the φ values of inclusion complexes.

Original languageEnglish
Pages (from-to)344-349
Number of pages6
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume114
DOIs
Publication statusPublished - 2013

Fingerprint

Sulfonic Acids
sulfonic acid
Cyclodextrins
Quantum yield
Naphthalene
naphthalene
Fluorescence
inclusions
fluorescence
Acids
augmentation
polarity
cucurbit(7)uril
cavities
Spectrophotometers
Moon
natural satellites
spectrophotometers
Complexation
Excited states

Keywords

  • Anilinonaphthalene sulfonic acid
  • Cucurbit[7]uril
  • Cyclodextrin
  • Fluorescence quantum yields
  • Inclusion complex

ASJC Scopus subject areas

  • Instrumentation
  • Atomic and Molecular Physics, and Optics
  • Analytical Chemistry
  • Spectroscopy

Cite this

The enhancement of fluorescence quantum yields of anilino naphthalene sulfonic acids by inclusion of various cyclodextrins and cucurbit[7]uril. / Sueishi, Yoshimi; Fujita, Tomonori; Nakatani, Shinichiro; Inazumi, Naoya; Osawa, Yoshihiro.

In: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, Vol. 114, 2013, p. 344-349.

Research output: Contribution to journalArticle

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abstract = "The association constants (K) for the inclusion complexation of four kinds of cyclodextrins (CDs (β- And γ-), 2,6-di-O-methylated β- CD, and 2,3,6-tri-O-methylated β- CD) and cucurbit[7]uril (CB[7]) with 1,8- And 2,6- Anilinonaphthalene sulfonic acids (ANSs) were determined from fluorescence spectra enhanced by inclusion. Various CDs and CB[7] form stable 1:1 inclusion complexes with 1,8- And 2,6-ANSs: K = 80-11700 M-1for 2,6-ANS and 50-195 M-1for 1,8-ANS. The high stability of the inclusion complexes of 2,6-ANS with CB[7] and 2,6-di-O-methylated b-CD is shown. Further, we determined the fluorescence quantum yields (φvalues) for the inclusion complexes of ANSs by using a fluorescence spectrophotometer equipped with a half-moon unit. Theφvalues of 1,8- And 2,6-ANSs were largely enhanced by the inclusion of methylated β-CDs and did not correlate with the degree of stability (K) of the inclusion complexes. We characterized the structures of the inclusion complexes by 2D ROESY-NMR measurements. In addition, the microenvironmental polarity inside the hydrophobic CD and CB[7] cavities was evaluated using the fluorescence probe 2,6-ANS. Based on the emission mechanism and the aspect of inclusion in a hydrophobic cavity, we have suggested that the microenvironmental polarity and viscosity for the excited state of ANS plays an important role for the φ values of inclusion complexes.",
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T1 - The enhancement of fluorescence quantum yields of anilino naphthalene sulfonic acids by inclusion of various cyclodextrins and cucurbit[7]uril

AU - Sueishi, Yoshimi

AU - Fujita, Tomonori

AU - Nakatani, Shinichiro

AU - Inazumi, Naoya

AU - Osawa, Yoshihiro

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