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When two atoms share electrons to complete their valence shells, they create a covalent bond. An atom's electronegativity—the force with which shared electrons are pulled towards an atom—determines how the electrons are shared. Molecules formed with covalent bonds can be either polar or nonpolar. Atoms with similar electronegativities form nonpolar covalent bonds; the electrons are shared equally. Atoms with different electronegativities share electrons unequally,...
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Covalent bonds are formed between two atoms when both have similar tendencies to attract electrons to themselves (i.e., when both atoms have identical or fairly similar ionization energies and electron affinities). Nonmetal atoms frequently form covalent bonds with other nonmetal atoms. For example, the hydrogen molecule, H2, contains a covalent bond between its two hydrogen atoms. When two separate hydrogen atoms with a particular potential energy approach each other, their valence orbitals...
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The molecular orbital theory describes the distribution of electrons in molecules in a manner similar to the distribution of electrons in atomic orbitals. The region of space in which a valence electron in a molecule is likely to be found is called a molecular orbital. Mathematically, the linear combination of atomic orbitals (LCAO) generates molecular orbitals. Combinations of in-phase atomic orbital wave functions result in regions with a high probability of electron density, while...
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Silane catecholates: versatile tools for self-assembled dynamic covalent bond chemistry.

Yoshiteru Kawakami1, Tsuyoshi Ogishima1, Tomoki Kawara1

  • 1Department of Chemistry, Faculty of Science, Kanagawa University, 2946, Tsuchiya, Hiratsuka 259-1293, Japan. kabe@kanagawa-u.ac.jp.

Chemical Communications (Cambridge, England)
|May 9, 2019
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Summary

Researchers created shape-persistent macrocycles and 3D nanocages using dynamic covalent chemistry. These structures can encapsulate ammonium ions, demonstrating their potential for molecular recognition and host-guest chemistry applications.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Dynamic covalent chemistry (DCC) enables the construction of complex molecular architectures.
  • Silane catecholates are versatile building blocks for supramolecular structures.
  • Macrocycles and nanocages offer unique cavities for molecular encapsulation.

Purpose of the Study:

  • To develop a one-pot method for synthesizing shape-persistent macrocycles and 3D nanocages.
  • To investigate the structural properties and stability of these novel architectures.
  • To explore the encapsulation capabilities of the macrocycles and nanocages for guest molecules, specifically ammonium ions.

Main Methods:

  • One-pot synthesis utilizing MeCN-promoted dynamic covalent bond formation.
  • Characterization of synthesized macrocycles and nanocages using X-ray crystallography.
  • Cation-exchange reactions to demonstrate host-guest interactions and encapsulation.

Main Results:

  • Successful synthesis of shape-persistent macrocycles and 3D nanocages from silane catecholates.
  • Structural confirmation of the macrocyclic and nanocage architectures via X-ray crystallography.
  • Demonstration of cation-exchange reactions and successful encapsulation of ammonium ions within anionic macrocycles and nanocages.

Conclusions:

  • The one-pot MeCN-promoted DCC approach is effective for constructing complex silane-based macrocycles and nanocages.
  • The synthesized structures exhibit shape persistence and possess cavities suitable for guest encapsulation.
  • These findings open avenues for designing novel host-guest systems and functional materials.