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Covalent Bonds01:29

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Covalent Bonds01:08

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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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Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual attraction of atoms for a “shared” pair of electrons.
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Chiral induction in covalent organic frameworks.

Xing Han1, Jie Zhang1, Jinjing Huang1

  • 1School of Chemistry and Chemical Engineering and State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai, 200240, China.

Nature Communications
|April 5, 2018
PubMed
Summary
This summary is machine-generated.

Researchers created chiral covalent organic frameworks (CCOFs) from achiral materials using chiral catalysts. These CCOFs show promise for enantioselective sensing and asymmetric catalysis.

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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Achieving synthetic control over chirality and function in covalent organic frameworks (COFs) remains a significant challenge.
  • Metal-organic frameworks have demonstrated advanced synthetic control, but COFs lag in this aspect.
  • Chiral catalysis offers a potential route to induce chirality in achiral precursors.

Purpose of the Study:

  • To demonstrate the crystallization of chiral covalent organic frameworks (CCOFs) from achiral organic precursors.
  • To achieve chiral control in COFs through chiral catalytic induction.
  • To explore the applications of these CCOFs in enantioselective sensing and asymmetric catalysis.

Main Methods:

  • Solvothermal synthesis of nine two-dimensional CCOFs using imine condensations.
  • Utilized C3-symmetric 1,3,5-triformylphloroglucinol (Tp) and various diamine or triamine linkers.
  • Employed catalytic amounts of (R)- or (S)-1-phenylethylamine to induce chirality.

Main Results:

  • Successfully synthesized nine homochiral CCOFs via chiral catalytic induction.
  • Homochirality arises from chiral catalyst-induced immobilization of propeller-like tris(N-salicylideneamine) cores.
  • The CCOF-TpTab exhibited high enantioselectivity for chiral carbohydrates and served as a heterogeneous catalyst for asymmetric Henry reactions after Cu(II) modification.

Conclusions:

  • Chiral catalytic induction is an effective strategy for synthesizing chiral COFs from achiral precursors.
  • The synthesized CCOFs possess inherent chirality and exhibit enantioselective properties.
  • These CCOFs are promising materials for chiral sensing and heterogeneous asymmetric catalysis.