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Chromophoric Water-Soluble Tetrakis(4-Carboxyphenylazo)-calix[4]arene: Binding of Arylammonium Ions and Benzene

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Abstract

The interaction of water-solubletetrakis(4-carboxyphenylazo)calix[4]arene with N,N,N trimethylarylammoniumiodides and benzene was investigated in order to correlate the effect ofanilinium salts on the binding properties of the cup-shaped hydrophobiccavity with the monolayer spreading behavior of a series of amphiphilicanalogs. Whereas multiple binding is observed for N,N,N-trimethylaniliniumiodide and benzene, NMR titration oftetrakis(4-carboxyphenylazo)calix[4]arene withN,N,N-trimethyl-N-(2-naphthyl)ammonium iodide indicates 2 : 1 complexationwithin the cavity of the calixarene with binding constants of K1 = 8024 M-1and K2 = 3134 M-1.

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Authors and Affiliations

  1. School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332-0400, U.S.A

    J. Cameron Tyson, David M. Collard & Kenneth D. Hughes

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  1. J. Cameron Tyson
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  2. David M. Collard
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  3. Kenneth D. Hughes
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Tyson, J.C., Collard, D.M. & Hughes, K.D. Chromophoric Water-Soluble Tetrakis(4-Carboxyphenylazo)-calix[4]arene: Binding of Arylammonium Ions and Benzene. Journal of Inclusion Phenomena 29, 109–118 (1997). https://doi.org/10.1023/A:1007969532541

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