Molecular recognition and self-assembly special feature: Encapsulation and characterization of proton-bound amine homodimers in a water-soluble, self-assembled supramolecular host.

ABSTRACT: Cyclic amines can be encapsulated in a water-soluble self-assembled supramolecular host upon protonation. The hydrogen-bonding ability of the cyclic amines, as well as the reduced degrees of rotational freedom, allows for the formation of proton-bound homodimers inside of the assembly that are otherwise not observable in aqueous solution. The generality of homodimer formation was explored with small N-alkyl aziridines, azetidines, pyrrolidines, and piperidines. Proton-bound homodimer formation is observed for N-alkylaziridines (R = methyl, isopropyl, tert-butyl), N-alkylazetidines (R = isopropyl, tert-butyl), and N-methylpyrrolidine. At high concentration, formation of a proton-bound homotrimer is observed in the case of N-methylaziridine. The homodimers stay intact inside the assembly ove

SUBMITTER: Pluth MD 

PROVIDER: S-EPMC2705522 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature