Supramolecular assembly of self-labeled amphicalixarenes.

The synthesis and precise supramolecular organization of new amphicalixarene 4 bearing four rodlike aligned fluorescent terephthalic benzamide moieties in the upper rim is reported. The aggregation of 4 was monitored by a combination of fluorescence, conductometry, and cryo-TEM measurements at different pH values and revealed significant structural differences. Most interestingly, we found that exactly 12 molecules of 4 assemble to form a spherical and structurally persistent micelle at pH 7, which coexists with rodlike micelles.

Pyrene binding to persistent micelles formed from a dendro-calixarene.

The formation of micelles of an amphiphilic dendro-calixarene (1) was studied using pyrene as a guest molecule. Steady-state fluorescence experiments were performed, which showed that pyrene is readily solubilized in the micelles and senses an environment with a moderate polarity. Time-resolved fluorescence measurements showed that pyrene in the micelles have two lifetimes, suggesting some compartmentalization of the guest within the micelles.