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Oxidation-Reduction Reactions03:11

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Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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After glycolysis, the charged pyruvate molecules enter the mitochondria via active transport and undergo three enzymatic reactions. These reactions ensure that pyruvate can enter the next metabolic pathway so that energy stored in the pyruvate molecules can be harnessed by the cells.
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Oxidative and reductive cyclization in stiff dithienylethenes.

Michael Kleinwächter1, Ellen Teichmann1, Lutz Grubert1

  • 1Department of Chemistry & IRIS Adlershof, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, 12489 Berlin, Germany.

Beilstein Journal of Organic Chemistry
|December 1, 2018
PubMed
Summary
This summary is machine-generated.

Stiff dithienylethenes exhibit electrochromism via oxidative cyclization. Ring size and substituents influence this process, with a rare reductive pathway observed for benzonitrile derivatives.

Keywords:
(spectro)electrochemistrydiaryletheneselectrochromismmolecular switches

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Area of Science:

  • Organic electrochemistry
  • Photochromic materials

Background:

  • Dithienylethenes are photochromic compounds known for reversible isomerizations.
  • Stiff dithienylethenes possess conformational constraints influencing their reactivity.
  • Electrochromism in dithienylethenes is typically induced by oxidation.

Purpose of the Study:

  • To investigate the electrochemical behavior of stiff dithienylethenes.
  • To explore the influence of ring size and substituents on electrocyclization.
  • To elucidate the mechanisms of oxidative and reductive electrocyclization pathways.

Main Methods:

  • Electrochemical analysis (cyclic voltammetry).
  • Synthesis of various stiff dithienylethene derivatives.
  • Spectroscopic characterization of isomers and products.

Main Results:

  • Electrochromism was observed in most stiff dithienylethene derivatives.
  • Oxidative cyclization of open isomers was the major electrochromic pathway.
  • Ring size affected cyclization: 6-membered rings cyclized from both E- and Z-isomers, while 7-membered rings only from Z-isomers.
  • Benzonitrile substituents enabled a rare reductive electrocyclization pathway for both stiff and normal dithienylethenes.

Conclusions:

  • Stiff dithienylethenes display tunable electrochromic properties.
  • The conformational rigidity and electronic effects of substituents significantly impact electrocyclization.
  • The discovery of reductive electrocyclization broadens the application potential of dithienylethene systems.