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Related Concept Videos

Electron Carriers01:24

Electron Carriers

90.5K
Electron carriers can be thought of as electron shuttles. These compounds can easily accept electrons (i.e., be reduced) or lose them (i.e., be oxidized). They play an essential role in energy production because cellular respiration is contingent on the flow of electrons.
Over the many stages of cellular respiration, glucose breaks down into carbon dioxide and water. Electron carriers pick up electrons lost by glucose in these reactions, temporarily storing and releasing them into the electron...
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Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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A new type of carborane-based electron-accepting material.

Sunhee Lee1, Jisu Shin, Doo-Hyun Ko

  • 1Department of Chemistry, Seoul Women's University, Seoul 01797, Republic of Korea. wshan@swu.ac.kr.

Chemical Communications (Cambridge, England)
|September 23, 2020
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Summary

Researchers developed a novel carborane-based electron acceptor by directly attaching an ethynyl group. This modification significantly alters the electrochemical properties of ortho-carborane systems.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Carboranes are a unique class of boron-containing compounds with diverse applications.
  • Electron acceptors are crucial components in various electronic and optoelectronic devices.
  • Modifying carborane structures can tune their electronic properties for specific applications.

Purpose of the Study:

  • To synthesize and characterize a new carborane-based electron acceptor.
  • To investigate the impact of direct ethynyl group attachment on carborane electronic properties.
  • To explore the potential of these modified carboranes in electronic applications.

Main Methods:

  • Synthesis of ethynyl-functionalized ortho-carboranes.
  • Photophysical analysis (e.g., UV-Vis absorption, fluorescence spectroscopy).
  • Electrochemical analysis (e.g., cyclic voltammetry).
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Successful preparation of a novel carborane-based electron acceptor with an ethynyl group directly attached to the carboranyl carbon.
  • Photophysical and electrochemical analyses revealed significant changes in electronic properties compared to unmodified carboranes.
  • DFT calculations confirmed the substantial influence of the ethynyl group on the electronic structure and properties of the ortho-carborane system.

Conclusions:

  • Direct ethynyl group attachment is an effective strategy for tuning the electrochemical properties of carborane-based electron acceptors.
  • These modified carboranes show promise for applications in organic electronics.
  • Further research can explore a wider range of functional groups and carborane scaffolds.