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

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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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan

    Yoshimi Sueishi, Yuki Matsumoto, Yuka Kimata & Tadashi Hanaya

  2. Otsuka Electronics Co. Ltd, 1-10 Sasagaoka, Minakuchi-cho, Kouka-shi, Shiga, 528-0061, Japan

    Yoshihiro Osawa

  3. Technical Support Division, Graduate School of Science, Osaka University, Toyonaka, Osaka, 560-0043, Japan

    Naoya Inazumi

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  1. Yoshimi Sueishi
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  2. Yuki Matsumoto
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  3. Yuka Kimata
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  4. Yoshihiro Osawa
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  6. Tadashi Hanaya
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Sueishi, Y., Matsumoto, Y., Kimata, Y. et al. Characterization of group-inclusion complexations of rhodamine derivatives with native and 2,6-di-O-methylated β-cyclodextrins. J Incl Phenom Macrocycl Chem 96, 365–372 (2020). https://doi.org/10.1007/s10847-020-00979-y

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