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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Mitochondrial precursors are partially unfolded or loosely folded polypeptide chains. Newly synthesized precursors are inhibited from spontaneously folding into their native conformation by the cytosolic chaperones, heat shock proteins 70 (Hsp70), and mitochondrial import stimulation factors (MSFs). Precursors bound to MSFs are guided to the TOM70-TOM37 receptors, while precursors bound to Hsp70  chaperones are targetted to TOM20-TOM22 receptor complexes.
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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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Halogens03:01

Halogens

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Brominated graphene as a versatile precursor for multifunctional grafting.

Heather Au1, Noelia Rubio1, Milo S P Shaffer1

  • 1Departments of Chemistry & Materials , Imperial College London , London , SW7 2AZ , UK .

Chemical Science
|April 10, 2018
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Summary

Researchers developed a new method to brominate few-layer graphene sheets (FLG-Br), creating a versatile precursor for graphene functionalization. This advancement enhances graphene

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Nanotechnology

Background:

  • Few-layer graphene (FLG) possesses unique properties but often suffers from poor solubility and dispersibility.
  • Direct functionalization of graphene is challenging, limiting its applications.
  • Developing stable, liquid-phase precursors is crucial for scalable graphene modification.

Purpose of the Study:

  • To develop a non-destructive chemical method for brominating FLGs.
  • To demonstrate the utility of brominated FLGs (FLG-Br) as a precursor for diverse graphene derivatives.
  • To enhance the solubility and dispersibility of graphene materials.

Main Methods:

  • Non-destructive chemical reduction and bromination of FLGs.
  • Characterization using X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis coupled with mass spectrometry (TGA-MS), and Raman spectroscopy.
  • Functionalization via atom transfer radical polymerization (ATRP) and nucleophilic substitution reactions.

Main Results:

  • Successful covalent attachment of bromine to FLGs, confirmed by XPS.
  • FLG-Br demonstrated as a stable, liquid-phase precursor for functionalized graphene.
  • Synthesis of poly(methyl methacrylate) (PMMA)-grafted graphene (FLG-PMMA) with sixfold increased dispersibility in acetone.
  • Preparation of methoxypolyethylene glycol (mPEG)- and OH-substituted graphene derivatives.
  • Grafting ratios (GR) ranged from 6% to 25%, with all derivatives showing improved solubility in organic solvents.

Conclusions:

  • The developed chemical reduction and bromination method offers a versatile route to functionalized graphene.
  • FLG-Br serves as an effective precursor for synthesizing various graphene derivatives with enhanced solubility.
  • This approach significantly improves graphene's processability for potential applications.