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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,...
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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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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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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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Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
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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.
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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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Porous Aromatic Frameworks (PAFs).

Yuyang Tian1, Guangshan Zhu1

  • 1Key Laboratory of Polyoxometalate Science of the Ministry of Education and Faculty of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China.

Chemical Reviews
|February 27, 2020
PubMed
Summary
This summary is machine-generated.

Porous aromatic frameworks (PAFs) are advanced porous solids with high surface areas and robust carbon-carbon bonds. This review details PAFs synthesis, functionalization, and applications, highlighting their unique stability and versatility.

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Area of Science:

  • Materials Science
  • Chemistry

Background:

  • Porous aromatic frameworks (PAFs) are a class of porous solids characterized by rigid frameworks and high surface areas.
  • They are constructed from aromatic building units linked by strong carbon-carbon bonds, offering unique chemical stability.

Purpose of the Study:

  • To provide a comprehensive review of the essential developments in the field of PAFs.
  • To elucidate the synthesis, functionalization, and applications of PAFs.

Main Methods:

  • Thematic review of existing literature on PAFs.
  • Explanation and exemplification of synthesis strategies.
  • Discussion of functionalization techniques and resulting properties.
  • Overview of diverse applications.

Main Results:

  • PAFs exhibit exceptional stability due to their carbon-carbon bonded aromatic structures.
  • Their functionalities can be inherent or introduced via postmodification.
  • PAFs offer advantages over traditional porous materials like zeolites and metal-organic frameworks in harsh environments.

Conclusions:

  • PAFs are a rapidly expanding research area with significant potential.
  • Understanding their synthesis, functionalization, and applications is crucial for future advancements.
  • The review summarizes current progress and offers a future outlook for PAF research.