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A reduction-oxidation reaction is commonly called a redox reaction. In a redox reaction, electrons are transferred from one species to another rather than being shared between or among atoms. The reducing agent or reductant is the species that loses electrons and gets oxidized in the process. The species that gains electrons and gets reduced in the process is the oxidizing agent or oxidant. Redox reactions are represented as two separate equations called half-reactions, where one equation...
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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
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Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Ladder diagrams are useful tools for understanding redox equilibrium reactions, especially the effects of concentration changes on the electrochemical potential of the reaction. The vertical axis in the redox ladder diagrams represents the electrochemical potential, E. The area of predominance is demarcated using the Nernst equation.
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Redox- and Protonation-Tunable Diboraheptacenes.

Jinhyo Hwang1, Heechan Kim1, João V Schober2

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139-4307, Massachusetts, United States.

Journal of the American Chemical Society
|February 26, 2026
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Summary

This study introduces diboraheptacenes, novel boron-doped acenes. These compounds exhibit tunable electronic properties and unique redox and protonation chemistry, paving the way for advanced organic electronics.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Acenes are key organic electronic materials due to their π-electron delocalization and small HOMO-LUMO gaps.
  • Incorporating heteroatoms into acenes allows tuning of electronic properties and introduces sites for chemical reactions.
  • The redox chemistry of boron-doped higher acenes is not well understood.

Purpose of the Study:

  • To synthesize and characterize diboraheptacenes.
  • To investigate the multistate redox and protonation chemistry of these novel compounds.
  • To establish the relationship between redox/protonation states and their electronic/photophysical properties.

Main Methods:

  • Synthesis of tetrahydrodiboraheptacene (1).
  • Generation of radical anion (1•−) via one-electron reduction.
  • Accessing fully aromatized diborataheptacene dianion (22−) via double deprotonation.
  • Characterization of redox-interconversion between benzenoid and quinoidal structures.
  • Spectroscopic analysis (UV-Vis, fluorescence) of dianion (22−) and neutral species (2).
  • Investigating reactivity with CO2, acrylonitrile, and H2O.

Main Results:

  • Synthesis and structural characterization of diboraheptacene derivatives.
  • Generation of radical anion and dianion species with distinct redox states.
  • Demonstration of redox-interconversion between benzenoid and quinoidal structures (22− to 2).
  • Diborataheptacene dianion (22−) exhibits NIR absorption (λabs = 951 nm) due to a small HOMO-LUMO gap.
  • Neutral diboraheptacene (2) displays red fluorescence (λem = 682 nm).
  • Dianion undergoes cycloaddition reactions and hydroxylation.

Conclusions:

  • Diboraheptacenes represent the first diboron-doped π-isosteres of all-hydrocarbon heptacene.
  • Redox and protonation state significantly influence electronic structure, photophysics, and reactivity.
  • These findings establish an extended diboraacene platform with tunable properties for organic electronics.