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Related Concept Videos

Network Covalent Solids02:18

Network Covalent Solids

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Network covalent solids contain a three-dimensional network of covalently bonded atoms as found in the crystal structures of nonmetals like diamond, graphite, silicon, and some covalent compounds, such as silicon dioxide (sand) and silicon carbide (carborundum, the abrasive on sandpaper). Many minerals have networks of covalent bonds.
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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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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Crystal Field Theory
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Related Experiment Video

Updated: May 6, 2026

Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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An azine-linked covalent organic framework.

Sasanka Dalapati1, Shangbin Jin, Jia Gao

  • 1Department of Materials Molecular Science, Institute for Molecular Science, National Institutes of Natural Sciences , 5-1 Higashiyama, Myodaiji, Okazaki 444-8787, Japan.

Journal of the American Chemical Society
|November 5, 2013
PubMed
Summary

New covalent organic frameworks (COFs) with pyrene columns exhibit high luminescence and porosity. These azine-linked COFs demonstrate exceptional sensitivity and selectivity for detecting explosives like 2,4,6-trinitrophenol.

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Area of Science:

  • Materials Science
  • Nanotechnology
  • Organic Chemistry

Background:

  • Covalent organic frameworks (COFs) are crystalline porous polymers with tunable structures.
  • Pyrene-based materials are known for their unique photophysical properties.
  • Developing robust and functional COFs for sensing applications remains a key challenge.

Purpose of the Study:

  • To synthesize novel two-dimensional covalent organic frameworks (COFs) using pyrene building blocks.
  • To investigate the structural, porosity, and photophysical properties of the resulting azine-linked COFs.
  • To evaluate the COFs' performance in chemosensing applications, particularly for explosive detection.

Main Methods:

  • Solvothermal condensation of hydrazine with 1,3,6,8-tetrakis(4-formylphenyl)pyrene.
  • Characterization using X-ray diffraction for crystallinity and structure determination.
  • Gas adsorption measurements to determine surface area and porosity.
  • Photoluminescence spectroscopy to assess luminescence properties.
  • Chemosensing experiments for selective detection of 2,4,6-trinitrophenol.

Main Results:

  • Highly crystalline two-dimensional azine-linked COFs were successfully synthesized.
  • The frameworks exhibit periodic ordering of pyrene columns and one-dimensional microporous channels.
  • The COFs possess permanent porosity, high surface area, and excellent chemical stability.
  • The pyrene columnar ordering leads to strong luminescence.
  • The azine units act as effective sites for hydrogen-bonding interactions.
  • The COFs demonstrated high sensitivity and selectivity for detecting 2,4,6-trinitrophenol (an explosive).

Conclusions:

  • The developed azine-linked pyrene COFs offer a promising platform for advanced materials.
  • Their unique structure, luminescence, and porosity enable highly sensitive and selective chemosensing.
  • This strategy can be extended to create diverse functional materials for various applications.