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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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, respectively.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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...

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Synthesis of Pyrrole-Sharing Fused Porphyrinoid Hybrids by Post-fabrication of Ni(II) Porphyrins.

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Di(p-dibenzi)[40]decaphyrin(1.0.0.0.0.1.0.0.0.0) Pd<sup>II</sup> Complex: A Weakly Hückel 38π-Aromatic Macrocycle.

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Related Experiment Video

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Hexaphyrin fused to two anthracenes.

Koji Naoda1, Hirotaka Mori, Naoki Aratani

  • 1Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, Japan.

Angewandte Chemie (International Ed. in English)
|August 7, 2012
PubMed
Summary

Researchers created a gold(III) complex with unique electronic properties. This novel material exhibits a sharp, near-infrared absorption band and significant two-photon absorption, making it promising for advanced optical applications.

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Published on: July 17, 2020

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Development of novel metal complexes for advanced applications.
  • Exploration of structure-property relationships in conjugated systems.
  • Investigating materials with strong optical absorption and nonlinear optical properties.

Purpose of the Study:

  • To synthesize and characterize a novel bis(gold(III)) complex.
  • To investigate the photophysical and electrochemical properties of the complex.
  • To evaluate its potential for applications in optics and electronics.

Main Methods:

  • Synthesis of a bis(gold(III)) complex incorporating 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoromethanesulfonyl (Tf) groups.
  • Characterization using spectroscopic and electrochemical techniques.
  • Measurement of optical absorption and two-photon absorption (TPA) cross-section.

Main Results:

  • The complex exhibits a sharp, red-shifted Q-band-like absorption at 1467 nm due to its planar, conjugated structure.
  • Multiple reversible redox potentials were observed, indicating tunable electronic properties.
  • A large two-photon absorption cross-section value was determined.

Conclusions:

  • The synthesized bis(gold(III)) complex possesses unique photophysical and electrochemical characteristics.
  • Its extended conjugation and planar structure are key to its remarkable optical properties.
  • The complex shows potential for applications requiring strong near-infrared absorption and nonlinear optical activity.