Structural aspects of marked difference in intramolecular exciplex emissions from self-complexes of β-cyclodextrins modified with (R) or (S)-1-(1-aminoethyl)naphthalene

Iwao Suzuki, Yuki Kato, Yuya Egawa, Jun ichi Anzai, Makoto Wadamori, Hideki Yokomizo, Keiko Takahashi

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Novel β-cyclodextrin (β-CyD) derivatives having an (R) or (S)-1-(1-aminoethyl)-naphthyl group exhibited red-shifted and structureless fluorescence and the normal fluorescence of the naphthyl group in alkaline aqueous solutions. The red-shifted fluorescence is attributed to the intramolecular exciplex. The intensity of the exciplex fluorescence is dependent on the chirality of the naphthyl group; the (S)-isomer emitted a stronger exciplex fluorescence than the (R)-isomer. From the NMR and circular dichroism spectral studies, the conformation of the intramolecular complexes of the (R)- and (S)-isomers is suggested; the naphthyl group of the (S)-isomer exists outside the β-CyD cavity, while the (R)-isomer is in the cavity. This conformational difference provides in the difference in the intramolecular exciplex formation.

Original languageEnglish
Pages (from-to)223-231
Number of pages9
JournalJournal of Molecular Structure
Volume602-603
DOIs
Publication statusPublished - 2002 Jan 9

Keywords

  • Cyclodextrin derivatives
  • Fluorescence spectroscopy
  • Intramolecular exciplex emission

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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