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Achieving Strong Positive Cooperativity through Activating Weak Non-Covalent Interactions.

Yan-Long Ma1,2, Hua Ke1, Arto Valkonen3

  • 1Department of Chemistry, South University of Science and Technology of China, Xueyuan Blvd 1088, Shenzhen, 518055, China.

Angewandte Chemie (International Ed. in English)
|November 16, 2017
PubMed
Summary

Synthetic molecular tubes exhibit strong positive cooperativity, achieving a record factor of 580 without ion pairing. This self-assembly behavior is driven by novel C-H⋅⋅⋅O hydrogen bonds, paving the way for advanced molecular construction.

Keywords:
cooperativityhost-guest chemistrymacrocyclesself-assemblysupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystal Engineering

Background:

  • Positive cooperativity is crucial in biological systems but challenging to achieve in synthetic molecular assemblies.
  • Weak non-covalent interactions are key to biological cooperativity, yet their synthetic exploitation remains limited.

Purpose of the Study:

  • To synthesize novel molecular tubes capable of high positive cooperativity.
  • To investigate the structural basis and magnitude of cooperativity in synthetic host-guest complexes.
  • To explore the potential of these complexes in constructing larger self-assembled structures.

Main Methods:

  • Synthesis of new syn-isomer molecular tubes.
  • Host-guest binding studies with DABCO-based organic cations.
  • X-ray single-crystal structure determination of the ternary complex.
  • Analysis of non-covalent interactions, specifically C-H⋅⋅⋅O hydrogen bonds.

Main Results:

  • The syn isomer of the molecular tubes selectively binds DABCO-based organic cations.
  • A ternary complex formed by two hosts and one guest exhibited exceptionally high positive cooperativity (α=580), the highest reported for synthetic systems without ion pairing.
  • X-ray crystallography revealed the formation of eight C-H⋅⋅⋅O hydrogen bonds between host molecules in the complex, which were absent in the free hosts.
  • The host-guest complex served as a building block for a [2+2] cyclic assembly.

Conclusions:

  • Novel molecular tubes can achieve significant positive cooperativity through the strategic formation of weak C-H⋅⋅⋅O hydrogen bonds.
  • This cooperativity surpasses previously reported synthetic systems lacking ion-pairing interactions.
  • The demonstrated self-assembly capability highlights the potential of these molecular tubes in constructing complex supramolecular architectures.