Synthesis and properties of shape-persistent macrocyclic amphiphiles with switchable amphiphilic portions

The bidirectional- and convergent-type syntheses of functionalized kinked p henyl-ethynyl oligomers containing ethynyl end groups are described. Key st eps in both approaches are the bromo-iodo selectivity of the Hagihara coupl ing and the possibility to deprotect acetylenes containing different silyl protective groups stepwise. Glaser coupling of the oligomeric bisacetylenes results in the corresponding macrocycles that contain polar and nonpolar s ide groups in a switchable arrangement.