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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.7K
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...
3.7K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

5.6K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
5.6K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.1K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.1K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.2K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

4.8K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction.
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction...
4.8K
Amino Acid Biosynthetic Pathways01:29

Amino Acid Biosynthetic Pathways

1.8K
Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which...
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Controlled Synthesis and Fluorescence Tracking of Highly Uniform PolyN-isopropylacrylamide Microgels
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Controlled Synthesis and Fluorescence Tracking of Highly Uniform PolyN-isopropylacrylamide Microgels

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Light-Gated Amine Exchange in Diarylethene-Crosslinked Microgels.

Kevin Broi1,2, Frédéric Grabowski1,2, Sarah Esser1,2

  • 1Institute of Technical and Macromolecular Chemistry, RWTH Aachen University, Worringerweg 2, 52074, Aachen, Germany.

Angewandte Chemie (International Ed. in English)
|August 23, 2025
PubMed
Summary

Researchers developed novel photo-responsive microgels capable of optically controlled uptake and release of functional amines, offering new possibilities for drug delivery systems.

Keywords:
ColloidsDiarylethenesDrug deliveryDynamic covalent chemistrySwitchable microgels

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Synthesis of Stimuli-responsive Nanogels using Aqueous One-step Crosslinking and Co-nanopolymerization
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Microfluidic Synthesis of Microgel Building Blocks for Microporous Annealed Particle Scaffold
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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Biotechnology

Background:

  • Microgels functionalized with photoswitchable groups are promising for multi-responsive systems, particularly in drug delivery.
  • Controlling the reversible uptake of functional molecules within microgels remains a significant challenge.

Purpose of the Study:

  • To develop a novel photo-responsive crosslinker for microgels to enable light-controlled molecule uptake and release.
  • To investigate the impact of photoisomerization and amine binding on microgel properties and responsiveness.

Main Methods:

  • Synthesis of poly(N-vinylcaprolactam)-based microgels crosslinked with a novel aniline-type diarylethene (DAE).
  • Utilizing UV and blue light irradiation to control the reversible exchange and covalent locking of primary amines within the microgels.
  • Characterization using dynamic light scattering and 19F NMR spectroscopy to confirm amine binding and assess microgel property changes.

Main Results:

  • Demonstrated light-controlled covalent binding of various amine derivatives (fluorinated, hydrophobic, hydrophilic) to the microgels.
  • Showcased remote control over microgel size, temperature, and pH responsiveness via light.
  • Confirmed reversible uptake and release of functional amines through optical gating.

Conclusions:

  • Developed a novel diarylethene crosslinker for creating multi-responsive microgels with optically controlled amine uptake and release.
  • Highlighted the potential of these photo-responsive microgels for advanced biological applications, including drug delivery.