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Aqueous Assembly of Zwitterionic Daisy Chains.

Yves Aeschi1,2, Sylvie Drayss-Orth1, Michal Valášek3

  • 1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 11, 2018
PubMed
Summary
This summary is machine-generated.

Researchers synthesized zwitterionic molecular daisy chains using a positively charged cyclophane and a negatively charged oligo(phenylene-ethynylene) (OPE) rod in water. The cyclic dimer [c2] was successfully isolated as interlocked species.

Keywords:
click-chemistrycyclophanedaisy chainhydrophobic complexationrotaxane

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Zwitterionic compounds possess unique charge distributions.
  • Molecular self-assembly is crucial for creating complex supramolecular structures.
  • Oligo(phenylene-ethynylene) (OPE) rods are versatile building blocks in molecular assembly.

Purpose of the Study:

  • To synthesize and characterize novel zwitterionic molecular [c2]- and [a2]-daisy chains.
  • To explore the self-assembly of these chains in aqueous media.
  • To investigate the formation of interlocked structures through recognition events.

Main Methods:

  • Synthesis of an acetylene-functionalized macrocyclic receptor.
  • Synthesis of a water-soluble OPE rod as a guest component.
  • Preparation of a heteroditopic daisy chain monomer.
  • Isolation of interlocked species via a stoppering reaction.
  • Characterization using 1H NMR spectroscopy.

Main Results:

  • Successful synthesis of a heteroditopic daisy chain monomer.
  • Strong aggregation of the monomer in a water/methanol mixture (4:1).
  • Formation of molecular daisy chains, isolated as interlocked species.
  • The cyclic dimer [c2] was the main product with a 30% isolated yield.
  • Characterization confirmed the cyclic dimer consisted of a mixture of diastereomers.

Conclusions:

  • The study demonstrates the successful synthesis of zwitterionic molecular daisy chains.
  • Host-guest recognition in aqueous media drives the formation of interlocked supramolecular architectures.
  • The described method provides a pathway for constructing complex molecular assemblies.