Resorcinarenes with 2-benzimidazolone bridges: self-aggregation, self-assembled dimeric capsules, and guest encapsulation.

ABSTRACT: The synthesis and spectroscopic characterization of self-assembled dimeric resorcinarenes 1a-d containing four 2-benzimidazolone (cyclic urea) bridges are reported. The nanometer-size capsules are held together by a cyclic array of complementary hydrogen bonds. Unlike the related imide-bridged resorcinarenes reported by Rebek and coworkers [Heinz, T., Rudkevich, D. M. & Rebek, J., Jr. (1998) Nature (London) 394, 764-766], these strongly bound dimers aggregate in chloroform solutions yielding different self-organized structures, depending on the nature and length of the four carbon chains attached at the bottom of each resorcinarene platform, as revealed by transmission electron microscopy. Thus, phenethyl groups (dimer 1c x 1c) produce long fibers, probably arising from tail to tail contac

SUBMITTER: Ebbing MH 

PROVIDER: S-EPMC122703 | biostudies-literature | 2002 Apr

REPOSITORIES: biostudies-literature