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Donor-acceptor ring-in-ring complexes.

Ross S Forgan1, Cheng Wang, Douglas C Friedman

  • 1Center for the Chemistry of Integrated Systems and Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3133, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 14, 2011
PubMed
Summary
This summary is machine-generated.

Researchers assembled donor-acceptor ring-in-ring complexes using cyclophanes and crown ethers. While these complexes form, CH···O interactions hinder the creation of molecular Borromean rings.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Self-assembly of mechanically interlocked molecules (MIMs) is crucial for advanced materials.
  • Donor-acceptor interactions are key for constructing complex supramolecular architectures.
  • Previous work has explored cyclophane-crown ether complexes for MIM synthesis.

Purpose of the Study:

  • To report the self-assembly of novel donor-acceptor ring-in-ring complexes.
  • To investigate the potential of these complexes as intermediates for molecular Borromean rings (BRs).
  • To understand the structural factors influencing the formation of higher-order MIMs.

Main Methods:

  • Synthesis of three donor-acceptor ring-in-ring complexes using a tetracationic cyclophane and functionalized crown ethers.
  • Characterization by 1H NMR spectroscopy to confirm 1:1 complex formation.
  • UV/Vis spectroscopy to measure binding constants via charge-transfer interactions.
  • X-ray crystallography to analyze solid-state structures and intermolecular interactions.

Main Results:

  • Successful formation of 1:1 ring-in-ring complexes between cyclobis(paraquat-4,4'-biphenylene) and dioxynaphthalene (DNP) or tetrathiafulvalene (TTF) containing crown ethers.
  • Binding constants up to 4×10^3 M^-1 were measured, indicating significant charge-transfer interactions.
  • X-ray crystallography revealed strong CH···O interactions that stabilize the complexes but mask recognition sites.
  • These interactions impede the necessary further steps for constructing molecular Borromean rings.

Conclusions:

  • Ring-in-ring complexes can be formed, but their utility as intermediates for Borromean rings is limited by stabilizing interactions.
  • The observed CH···O interactions highlight challenges in designing MIMs with multiple recognition sites.
  • Orthogonality of recognition motifs is critical for the stepwise synthesis of complex MIMs.
  • Future designs may require longer polyether loops to overcome steric hindrance and facilitate further assembly.