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π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

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Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the...
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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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MO Theory and Covalent Bonding02:40

MO Theory and Covalent Bonding

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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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Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.6K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the...
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π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each...
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Newman Projections02:06

Newman Projections

17.0K
Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as...
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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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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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Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds.

Jia Guo1, Yanhong Xu, Shangbin Jin

  • 11] Department of Materials Molecular Science, Institute for Molecular Science, National Institutes of Natural Sciences, 5-1 Higashiyama, Myodaiji, Okazaki 444-8787, Japan [2] State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200433, China.

Nature Communications
|November 14, 2013
PubMed
Summary

Chemically stable covalent organic frameworks with extended π-conjugation were developed. These novel porous materials exhibit enhanced electronic properties, enabling applications in photoswitches and photovoltaic cells.

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

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent organic frameworks (COFs) are crystalline porous materials.
  • Existing COFs often suffer from chemical instability and limited π-conjugation.
  • These limitations hinder their application in advanced electronic devices.

Purpose of the Study:

  • To design and synthesize a chemically stable, electronically conjugated organic framework.
  • To investigate the structural and electronic properties of the novel COF.
  • To explore the potential applications of this COF in electronic devices.

Main Methods:

  • Utilizing π-π-stacking interactions for framework assembly.
  • Topological design of wire frameworks with ordered nanochannels.
  • Characterization of chemical stability, π-conjugation, and electronic properties.

Main Results:

  • A chemically stable, electronically conjugated organic framework was successfully synthesized.
  • The framework exhibits inborn periodic ordering of conjugated chains in 3D.
  • Demonstrated high on-off ratio photoswitches and efficient photovoltaic cells.

Conclusions:

  • The developed COF overcomes the limitations of traditional frameworks.
  • This work presents a strategy for creating ordered semiconducting porous materials.
  • The findings pave the way for innovations based on 2D extended π systems.