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Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Physical Properties of Amines

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

Anionic Chain-Growth Polymerization: Overview

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

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Updated: Jun 1, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Published on: April 19, 2019

Carborane-containing poly(fluorene): response to solvent vapors and amines.

Joseph J Peterson¹, Andrew R Davis, Mathias Werre

¹Polymer Science and Engineering Department, University of Massachusetts-Amherst, 120 Governors Drive, Amherst, Massachusetts 01003-9263, USA.

ACS Applied Materials & Interfaces

|May 20, 2011

Summary

Hybrid conjugated polymers with carborane show promise for organic electronics. These poly(fluorene) materials act as vapochromatic photoluminescent sensors for detecting volatile organic molecules.

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Area of Science:

Materials Science
Organic Electronics
Polymer Chemistry

Background:

Hybrid conjugated polymers with carborane units offer unique electronic properties.
Carborane's cage structure and bent geometry are advantageous for sensing applications.
Poly(fluorene) derivatives are known for their tunable photoluminescent properties.

Purpose of the Study:

To investigate the potential of poly(fluorene) containing o-carborane in the backbone as a sensor material.
To explore the vapochromatic and photoluminescent sensing capabilities of these hybrid polymers.
To demonstrate the application of these materials in detecting volatile organic molecules.

Main Methods:

Synthesis of hybrid conjugated polymers incorporating o-carborane into the poly(fluorene) backbone.
Fabrication of polymer films for sensor applications.
Characterization of photoluminescent properties and response to volatile organic compounds.

Main Results:

Poly(fluorene) films with o-carborane in the backbone exhibited vapochromatic behavior.
The photoluminescence of the polymer films was modulated by interactions with volatile organic molecules.
These materials demonstrated effective sensing capabilities for specific volatile organic compounds.

Conclusions:

Hybrid conjugated polymers based on poly(fluorene) and o-carborane function as effective vapochromatic photoluminescent sensors.
The unique properties of carborane contribute to the sensing mechanism.
These materials represent a novel class of sensors for volatile organic molecule detection in organic electronics.