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Chem Asian J. 2018 Apr 4;13(7):815-821. doi: 10.1002/asia.201800011. Epub 2018 Mar 2.

Integrative Self-Sorting: One-Pot Synthesis of a Hetero[4]rotaxane from a Daisy-Chain-Containing Hetero[4]pseudorotaxane.

Author information

1
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237, China.

Abstract

The structural complexity of mechanically interlocked molecules are very attractive to chemists owing to the challenges they present. In this article, novel mechanically interlocked molecules with a daisy-chain-containing hetero[4]rotaxane motif were efficiently synthesized. In addition, a novel integrative self-sorting strategy is demonstrated, involving an ABB-type (A for host, dibenzo-24-crown-8 (DB24C8), and B for guest, ammonium salt sites) monomer and a macrocycle host, benzo-21-crown-7 (B21C7), in which the assembled species in hydrogen-bonding-supported solvent only includes a novel daisy-chain-containing hetero[4]pseudorotaxane. The found self-sorting process involves the integrative recognition between B21C7 macrocycles and carefully designed components simultaneously containing two types of secondary ammonium ions and a host molecule, DB24C8 crown ether. The self-sorting strategy is integrative to undertake self-recognition behavior to form one single species of pseudorotaxane compared with the previous report. This self-sorting system can be used for the efficient one-pot synthesis of a daisy-chain-containing hetero[4]rotaxane in a good yield. The structure of hetero[4]rotaxane was confirmed by 1 H NMR spectroscopy and high-resolution electrospray ionization (HR-ESI) mass spectrometry.

KEYWORDS:

click chemistry; daisy chain; integrative self-sorting; one-pot synthesis; rotaxane

PMID:
29424064
DOI:
10.1002/asia.201800011

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