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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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The electron transport chain (ETC) is a crucial metabolic pathway that facilitates energy conversion in prokaryotic and eukaryotic cells. In eukaryotes, the ETC comprises four membrane-associated protein complexes in the inner mitochondrial membrane. In prokaryotes, the ETC in the plasma membrane can vary in composition, with fewer or different complexes depending on the organism and environmental conditions. These complexes transfer electrons from electron donors, such as NADH and FADH2, to...
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During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
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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.
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Catalytic electron drives host-guest recognition.

Yoshihiro Owatari1, Shuta Iseki1, Daiji Ogata1

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Electron injection initiates catalytic chain reactions, converting a non-planar molecule into a planar one. This process enables electron-triggered molecular recognition and host-guest complex formation.

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Area of Science:

  • Electrochemistry
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Electron injection can initiate chemical transformations.
  • Charge-transfer (CT) interactions are crucial in molecular recognition.
  • Controlling molecular geometry is key for host-guest complex formation.

Purpose of the Study:

  • To demonstrate electron injection triggering electrocatalytic chain reactions.
  • To achieve catalytic electron-triggered charge-transfer (CT) complex formation.
  • To develop a one-electron switch for molecular recognition.

Main Methods:

  • One-electron reduction of a hydroxy anthrone derivative (AQH-CH2CN) using electrocatalysis.
  • Formation of a stable anthraquinone radical anion (AQ•−).
  • Subsequent electron transfer and oxidation steps to form planar anthraquinone (AQ).

Main Results:

  • Electrocatalytic chain reactions convert AQH-CH2CN to AQ and acetonitrile (CH3CN).
  • The process is mild, sustainable, and uses a catalytic amount of electrons.
  • Conversion to planar AQ enables CT interaction and host-guest complex formation with U H Ant2.

Conclusions:

  • Sustainable electrocatalytic chain reactions can control CT interactions.
  • A one-electron switch is achieved, enabling catalytic electron-triggered turn-on molecular recognition.
  • This work offers a novel method for controlling supramolecular assembly through electrochemistry.