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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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.
Due to the absence of continuous...
2.9K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.1K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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.
Removing one hydrogen from the intervening CH2 group...
2.9K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.3K
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 double...
5.3K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

2.8K
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the...
2.8K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.4K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.4K

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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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2D Covalent Organic Frameworks Based on Heteroacene Units.

Fu Guo1, Weifeng Zhang2,3, Shuai Yang2,3

  • 1School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing, 100083, P. R. China.

Small (Weinheim an Der Bergstrasse, Germany)
|January 27, 2023
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Summary

Heteroacene-based covalent organic frameworks (COFs) offer enhanced stability and π-conjugation. This review summarizes their linkages, building blocks, and applications, paving the way for improved COF design.

Keywords:
covalent organic frameworksdesign and synthesisheteroacenes unitslinkagesperformance modulation

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent organic frameworks (COFs) are crystalline porous polymers with tunable properties.
  • Traditional COFs often lack sufficient π-π interactions and chemical stability.
  • Heteroacene units offer advantages due to their rigidity, π-conjugation, and electronic properties.

Purpose of the Study:

  • To review the advancements in heteroacene-based COFs.
  • To summarize linkage types and building blocks.
  • To highlight applications and future research directions.

Main Methods:

  • Literature review of heteroacene-based COFs.
  • Analysis of linkage strategies (reversible and irreversible).
  • Categorization of building blocks and their functionalities.

Main Results:

  • Heteroacene-based COFs exhibit enhanced physicochemical robustness and π-conjugation.
  • These materials overcome limitations of traditional COFs regarding π-π interactions and stability.
  • Diverse building blocks and linkage modes enable tailored COF properties.

Conclusions:

  • Heteroacene-based COFs represent a significant breakthrough in porous materials.
  • Their design offers improved control over complexity and functionality.
  • Further research can unlock new applications through optimized synthesis and building block selection.