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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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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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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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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...
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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

4.1K
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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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.
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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Oligomeric ferrocene rings.

Michael S Inkpen1, Stefan Scheerer2, Michael Linseis2

  • 1Department of Chemistry, Imperial College London, London SW7 2AZ, UK.

Nature Chemistry
|August 25, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel cyclic ferrocene oligomers, creating uniformly charged nanorings. These unique nanoscale materials exhibit well-defined redox behavior, paving the way for new electronic applications.

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Area of Science:

  • Supramolecular Chemistry
  • Nanomaterials Science
  • Organometallic Chemistry

Background:

  • Cyclic oligomers with redox-active units are highly sought-after nanoscale materials.
  • The synthesis and properties of such ferrocene-based rings were previously unexplored.

Purpose of the Study:

  • To synthesize and characterize the first family of cyclic ferrocene oligomers.
  • To investigate the electrochemical properties and electronic interactions within these novel nanostructures.

Main Methods:

  • Synthesis of differently sized ferrocene rings (cyclo[n], n=5-7, 9) with covalent Cp-Cp linkages.
  • Electrochemical analysis using solution voltammograms to observe redox behavior.
  • Theoretical calculations to correlate ring size, charge state, and interaction energies.

Main Results:

  • Successfully synthesized and characterized cyclic ferrocene oligomers (cyclo[n], n=5-7, 9).
  • Observed well-resolved, separated one-electron (1e-) redox waves due to close proximity of ferrocene units.
  • Demonstrated linear scaling of interaction free energies with ring charge and fast intramolecular electron transfer (∼10^7 s^-1).

Conclusions:

  • These molecules represent a new class of uniformly charged nanorings (diameter ∼1-2 nm).
  • The findings facilitate theoretical studies on charge distribution and electron transfer in nanoscale systems.