Synthesis and complexation of amphiphilic calix[4]arene phosphonates with organic molecules in solutions and Langmuir-Blodgett films

Synthesis and complexation of amphiphilic calix[4]arene phosphonates with organic molecules in solutions and Langmuir-Blodgett films

A family of amphiphilic alkoxycalix[4]arenes bearing phosphonyl groups directly attached to para positions of the aromatic rings is synthesized by the Arbuzov reaction of para-bromoalkoxycalix[4]arenes with alkyl esters of phosphorus (III) acid in the presence of NiBr 2. Amphiphilicity of the calixa...

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Bibliographic Details
Published in:Journal of molecular liquids Vol. 159; no. 2; pp. 117 - 123
Main Authors: Solovyov, A.V., Cherenok, S.O., Kalchenko, O.I., Atamas, L.I., Kazantseva, Z.I., Koshets, I.A., Tsymbal, I.F., Kalchenko, V.I.
Format: Journal Article
Language:English
Published: Elsevier B.V 01-03-2011
Subjects:
Association constants
Calixarenes
Langmuir-Blodgett films
Organophosphorus compounds
Supramolecular complexes
Organophosphorus compounds
Langmuir-Blodgett films
Calixarenes
Supramolecular complexes
Association constants
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Summary:A family of amphiphilic alkoxycalix[4]arenes bearing phosphonyl groups directly attached to para positions of the aromatic rings is synthesized by the Arbuzov reaction of para-bromoalkoxycalix[4]arenes with alkyl esters of phosphorus (III) acid in the presence of NiBr 2. Amphiphilicity of the calixarene phosphonates is controlled by varying the quantities of the hydrophilic phosphoryl groups at the upper rim and the hydrophobic alkyl groups at the lower rim. Complexation of the calixarenes with benzene derivatives and iso-butanol in solutions is studied by RP HPLC and IR spectroscopy methods. Langmuir-Blodgett films of the calixarene phosphonates are prepared. Physical characteristics and complexation of the films with volatile organic molecules are characterized. ► A family of the cone shaped amphiphilic calix[4]arene phosphonates is synthesized. ► Complexation of the calixarenes with benzene derivatives is studied by HPLC methods. ► Stability constants of the host – guest complexes are determined. ► Langmuir-Blodgett films of the calixarene phosphonates are prepared. ► Complexation of the LB films with volatile organic molecules are investigated.
ISSN:0167-7322
1873-3166
DOI:10.1016/j.molliq.2010.12.007