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One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy.

ABSTRACT: The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB24C8) based [c2]daisy chain structure and is ended with a benzo-21-crown-7 (B21C7) based rotaxane at each side. The key to the design involved encoding the selective threading using a steric hindrance-related "language", where highly selective self-assemblies occurred in a three-component self-sorting process, which included the threading of a benzylalkylammonium into a B21C7 and interpenetrated dimerized formation of a DB24C8 based [c2]daisy chain simultaneously; the precise pre-assembled system resulted in the efficient synthesis of hetero[4]rotaxane with a high-level of structural complexity under the "CuAAC" reaction.

SUBMITTER: Fu X

PROVIDER: S-EPMC5535066 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy.

Fu Xin X Zhang Qi Q Rao Si-Jia SJ Qu Da-Hui DH Tian He H

Chemical science 20160112 3

The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB24C8) based [c2]daisy chain structure and is ended with a benzo-21-crown-7 (B21C7) based rotaxane at each side. The key to the design involved encoding the selective threading usin ...[more]

PMID: 28808537

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