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Pseudo[3]rotaxane Type Compelxation between α- and β-Cyc1odextrins and N,N′-Dsiheptyl-4,4′-bipyridinium

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Abstract

Pseudo[3]rotaxane type complexation of α- and β-cyclodextrins (α- and β-CDs, respectively) with N,N′-Diheptyl-4,4′-bipyridinium (diheptyl viologen; HV2+) was investigated. A spectral displacement method using p-nitrophenol as a dye revealed that α-CD and HV2+ formed a 2:1 host-guest complex with stability constants being 3280 and 976 M−1 as the first and second steps of complexation, respectively. 1H-NMR spectra strongly indicated that α-CD accommodated the heptyl groups of HV2+. Although previous studies based on circular dichroism spectroscopy suggested the primary hydroxy side of α-CD faced to the positively charged bipyridinium moiety od HV2+, 2D-NMR studies clearly demonstrated that the secondary hydroxy side of α-CD faced to the bipyridinium moiety. β-CD also formed a 2:1 complex with HV2+ with a similar fashion.

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Abbreviations

CD:

cyclodextrin

cd:

circular dichroism

COSY:

correlation spectroscopy

HV2+ :

N,N′-diheptyl-4,4′-bipyridinium

NOE:

nuclear Overhauser effect

NMR:

nuclear magnetic resonance

pNP:

p-nitrophenol

ROESY:

rotating frame nuclear Overhauser effect spectroscopy

UV:

ultraviolet

1D:

one-dimensional

2D:

two-dimensional

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Tohoku University Aramaki, Aoba-ku, 980-8578, Sendai, Japan

    Iwao Suzuki & Akiyo Yamauchi

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  1. Iwao Suzuki
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  2. Akiyo Yamauchi
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Correspondence to Iwao Suzuki.

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Suzuki, I., Yamauchi, A. Pseudo[3]rotaxane Type Compelxation between α- and β-Cyc1odextrins and N,N′-Dsiheptyl-4,4′-bipyridinium. J Incl Phenom Macrocycl Chem 54, 193–200 (2006). https://doi.org/10.1007/s10847-005-7367-8

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  • DOI: https://doi.org/10.1007/s10847-005-7367-8

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