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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.4K
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...
4.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.4K
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...
4.4K
Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

16.9K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
16.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

8.0K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
8.0K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

6.1K
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,...
6.1K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

2.1K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
2.1K

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Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Aromaticity Switching in Porphyrinoids.

Miłosz Pawlicki1, Lechosław Latos-Grażyński2

  • 1Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50383, Wrocław. milosz.pawlicki@chem.uni.wroc.pl.

Chemistry, an Asian Journal
|March 18, 2015
PubMed
Summary

Porphyrinoids can switch between aromatic and antiaromatic states using modulators like redox or acid-base chemistry. This controllable electronic transformation offers potential for developing switchable optoelectronic materials.

Keywords:
NMR spectroscopyantiaromaticityaromaticitynuclear-independent chemical shiftporphyrinoids

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Porphyrinoids are macrocyclic compounds with tunable electronic properties.
  • Aromaticity in porphyrinoids can be modulated through external stimuli.
  • Understanding these modulations is key to designing advanced functional materials.

Purpose of the Study:

  • To review the reversible alteration of porphyrinoid aromaticity.
  • To highlight the role of modulators in switching electronic structures.
  • To explore the potential of switchable porphyrinoids in optoelectronics.

Main Methods:

  • Discussion of redox processes as electronic modulators.
  • Analysis of acid-base chemistry in altering aromaticity.
  • Examination of conformational changes influencing electronic states.

Main Results:

  • Porphyrinoid electronic structures can be reversibly modified.
  • Single macrocyclic frameworks can switch between diatropic and paratropic characteristics.
  • These transformations are readily and mutually exchangeable.

Conclusions:

  • Reversible switching of aromaticity in porphyrinoids is achievable.
  • Modulators like redox and acid-base chemistry are effective.
  • Switchable porphyrinoids are promising for constructing optoelectronic devices.