Characterization of group-inclusion complexations of rhodamine derivatives with native and 2,6-di-O-methylated β-cyclodextrins

Yoshimi Sueishi, Yuki Matsumoto, Yuka Kimata, Yoshihiro Osawa, Naoya Inazumi, Tadashi Hanaya

Research output: Contribution to journalArticlepeer-review

Abstract

The inclusion complexations of rhodamine derivatives with native and 2,6-di-O-methylated β-cyclodextrins (β-CD and DM-β-CD) were studied spectrophotometrically. Rhodamine derivatives were shown to form 1:1 inclusion complexes with β-CDs by the continuous variation method. The structures of the inclusion complexes were characterized by 1H-1H rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR measurements. It was found that native β-CD encapsulates the xanthenyl ring of rhodamines into the cyclodextrin cavity, while DM-β-CD forms two group-in complexes (phenyl-in and xanthenyl-in (bidirectional (bimodal) inclusion complexes)) with rhodamines bearing moderately bulky functional groups. Furthermore, we demonstrated the unique thermodynamics for the group-inclusion complex formation by DM-β-CD. The quantum yields for the inclusion complexes of rhodamines were determined using a quantum measurement apparatus equipped with a half-moon unit. The results indicated that the cyclodextrin inclusion of rhodamines with the bulky amino substituents on the xanthenyl ring largely decreases the quantum yield values. Based on these results, the substituent effects on the fluorescence process for the cyclodextrin inclusion complexes of rhodamines were discussed. This study provides useful insights for the functional group recognition of native and modified β-CDs.

Original languageEnglish
Pages (from-to)365-372
Number of pages8
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume96
Issue number3-4
DOIs
Publication statusPublished - Apr 1 2020

Keywords

  • Group-inclusion complex
  • Quantum yield
  • Rhodamine dye
  • Substituent effect
  • β-Cyclodextrins

ASJC Scopus subject areas

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

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