Synthesis and self-assembly properties of para-acyl-calix[8]arenes

The synthesis and interfacial assembly properties of a series of five para-acyl-calix[8]arenes are described, the products are obtained in good yields and all form stable monolayers at the air–water interface. The synthesis of a series of novel para-acyl-calix[8]arenes is described, while for acyl c...

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Published in:Tetrahedron letters 2007-07, Vol.48 (31), p.5503-5506
Main Authors: Jebors, Saïd, Ananchenko, Gennady S., Coleman, Anthony W., Ripmeester, John A.
Format: Article
Language:English
Subjects:
Acylation
Amphiphilic
Biochemistry, Molecular Biology
Calix-arenes
Langmuir
Life Sciences
Monolayer
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description The synthesis and interfacial assembly properties of a series of five para-acyl-calix[8]arenes are described, the products are obtained in good yields and all form stable monolayers at the air–water interface. The synthesis of a series of novel para-acyl-calix[8]arenes is described, while for acyl chain lengths of greater than eight carbon atoms total substitution at the para position occurs, in contrast to the para-acyl-calix[4]arenes, some esterification at the phenolic face may also occur, particularly for shorter acyl chain lengths. Simple saponification with potassium hydroxide in ethanol allows the pure compounds to be obtained in good yields. All the derivatives show amphiphilic behaviour with formation of stable monolayers at the air–water interface and apparent molecular areas between 150 and 275 Å 2.
doi_str_mv 10.1016/j.tetlet.2007.05.169
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subjects Acylation
Amphiphilic
Biochemistry, Molecular Biology
Calix-arenes
Langmuir
Life Sciences
Monolayer
title Synthesis and self-assembly properties of para-acyl-calix[8]arenes
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