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Related Concept Videos

Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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 overlap of p...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
NMR Spectroscopy of Aromatic Compounds01:14

NMR Spectroscopy of Aromatic Compounds

Aromatic compounds can be identified or analyzed using proton NMR and carbon‐13 NMR. Typically, aromatic hydrogens or hydrogens directly bonded to the aromatic rings are strongly deshielded by the aromatic ring current. Therefore, they absorb in the range of 6.5–8.0 ppm in proton NMR spectra. For instance, aromatic hydrogens directly bonded to the benzene ring absorb at 7.3 ppm. However, aromatic hydrogens of larger rings absorb farther upfield or downfield than the ideal range. Consider...

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Updated: Jun 23, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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BN-embedded aromatic hydrocarbons: synthesis, functionalization and applications.

Qiang Feng1, Ying Zhou1, Han Xu1

  • 1College of Chemistry and Chemical Engineering, Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang Key Laboratory of Organosilicon Chemistry and Application. Jiujiang University, Jiujiang 332005, China. huanan200890@163.com.

Chemical Society Reviews
|May 20, 2025
PubMed
Summary
This summary is machine-generated.

Replacing carbon-carbon bonds with boron-nitrogen bonds in polycyclic aromatic hydrocarbons (PAHs) creates advanced organic materials. This review explores BN-fused hydrocarbons, their synthesis, properties, applications, and the role of computational chemistry.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are foundational organic materials.
  • Substituting C-C bonds with B-N bonds in PAHs offers unique electronic, optical, and stability properties.
  • BN-fused aromatic hydrocarbons present opportunities for novel functional materials.

Purpose of the Study:

  • To provide a comprehensive review of BN-fused aromatic hydrocarbons.
  • To highlight synthetic strategies, fundamental properties, and emerging applications.
  • To emphasize the role of computational chemistry in material design and optimization.

Main Methods:

  • Literature review of recent advancements in BN-fused aromatic hydrocarbons.
  • Analysis of synthetic methodologies and structure-property relationships.
  • Discussion of computational chemistry's contribution to material discovery.

Main Results:

  • BN-fused aromatic hydrocarbons exhibit tunable photophysical and electronic properties.
  • Diverse synthetic routes enable precise molecular tailoring.
  • Emerging applications span organic optoelectronics and biomedicine.

Conclusions:

  • BN-fused aromatic hydrocarbons are promising for advanced functional materials.
  • Overcoming synthetic challenges is key to practical applications.
  • Interdisciplinary collaboration is crucial to unlock the potential of azaborinine chemistry.