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

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 Å2.