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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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.
Removing one hydrogen from the intervening CH2 group...
3.4K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.3K
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,...
4.3K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.1K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.4K
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...
3.4K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.4K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.4K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Pentacene-fused diporphyrins.

Lin Jiang1, James T Engle, Ross A Zaenglein

  • 1Department of Chemistry and Biochemistry, Miami University, Oxford, OH 45056 (USA).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 5, 2014
PubMed
Summary

Researchers synthesized novel fused porphyrin systems, revealing unique electronic interactions and enhanced stability. These multichromophoric molecules exhibit promising properties for advanced electronic and photophysical applications.

Keywords:
density functional calculationsmagnetic circular dichroism spectroscopyorganic electronicspentacenesporphyrin dimersπ-extended porphyrins

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Spectroscopy

Background:

  • Porphyrins and polycyclic aromatic hydrocarbons (PAHs) are crucial chromophores.
  • Designing extended π-conjugated systems is key for novel optoelectronic properties.
  • Understanding interchromophore electronic communication is vital for functional materials.

Purpose of the Study:

  • To synthesize and characterize novel pentacene-fused porphyrin dimers and quinone-fused dinaphthoporphyrins.
  • To investigate the electronic interactions within these multichromophoric systems.
  • To evaluate the stability and potential applications of these extended π-systems.

Main Methods:

  • Multistep organic synthesis of complex fused porphyrin structures.
  • Spectroscopic characterization including UV-visible absorption, emission, and magnetic circular dichroism (MCD).
  • Density Functional Theory (DFT) calculations for electronic structure analysis (HOMO/LUMO delocalization).

Main Results:

  • Successful synthesis of linearly conjugated pentacene-fused porphyrin dimers and cross-conjugated quinone-fused dinaphthoporphyrins.
  • Observed non-typical UV-visible absorptions indicating strong electronic coupling.
  • Spectroscopic data and DFT calculations confirm extensive HOMO and LUMO delocalization across the molecular framework.
  • The pentacene-fused porphyrin dimer demonstrated superior stability compared to related PAHs.

Conclusions:

  • The synthesized fused porphyrins are highly electronically interactive multichromophoric systems.
  • These molecules exhibit unique photophysical properties due to extended π-conjugation.
  • The enhanced stability and electronic properties position these systems for future applications in organic electronics and photonics.