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Related Concept Videos

Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Amino acids03:42

Amino acids

Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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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Pyrylium monolayers as amino-reactive platform.

Francesca A Scaramuzzo1, Arántzazu González-Campo, Chien-Ching Wu

  • 1Molecular Nanofabrication Group, University of Twente, P.O. Box 217, 7500 AE, Enschede, The Netherlands.

Chemical Communications (Cambridge, England)
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Summary

A novel pyrylium-based monolayer platform enables amine-terminated molecule immobilization. Successful binding is confirmed by a detectable switch in the monolayer

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Area of Science:

  • Materials Science
  • Surface Chemistry
  • Bioconjugation

Background:

  • Development of sensitive platforms for biomolecule detection is crucial.
  • Existing methods for immobilizing amine-terminated molecules can be complex.
  • Pyrylium chemistry offers unique reactive properties.

Purpose of the Study:

  • To introduce a new pyrylium-based monolayer platform.
  • To demonstrate its reactivity with amine-terminated molecules.
  • To establish a fluorescence-based readout for successful immobilization.

Main Methods:

  • Synthesis of a pyrylium-based monolayer.
  • Exposure of the monolayer to amine-terminated (bio)molecules.
  • Monitoring of fluorescence property changes.

Main Results:

  • The pyrylium monolayer exhibits reactivity towards amine-terminated molecules.
  • Immobilization of these molecules induces a distinct change in fluorescence.
  • This fluorescence switch serves as a reliable indicator of successful binding.

Conclusions:

  • The pyrylium monolayer platform provides an effective method for immobilizing amine-terminated (bio)molecules.
  • The fluorescence switch offers a simple and sensitive detection mechanism.
  • This platform has potential applications in biosensing and surface functionalization.