Guest recognition with micelle-bound cavitands

Abstract

We report that a benzimidazole cavitand is incorporated in aqueous phosphocholine (PC) micelles, folds into the vase conformation, and functions as small-molecule host. As a micelle-bound host it has the ability to sequester selective hydrophobic guest "anchors" into its interior. These anchors include cycloalkanes, adamantanes, and nitrogen heterocycles that compete favorably with the large excess of PC alkyl side-chains that make up the micelle interior. The adamantyl anchor was further functionalized with a fluorophore, and in another instance a dipeptide and both guests retain their recognition properties with the micelle-bound cavitand. Additionally, we report that variations in the cavitand periphery and rim are well-tolerated under our experimental conditions. We find that enhanced binding toward certain guests in both micelles as well as in solution occurs in response to titration with base; this previously unknown property of benzimidazole cavitands is reported in detail.