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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.9K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.9K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.8K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.8K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.1K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
3.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.4K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.8K
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.
7.8K

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Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications
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Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications

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Mechanism-Based Fluorogenic trans-Cyclooctene-Tetrazine Cycloaddition.

Arcadio Vázquez1, Rastislav Dzijak1, Martin Dračínský1

  • 1Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 2, 166 10, Prague, Czech Republic.

Angewandte Chemie (International Ed. in English)
|December 28, 2016
PubMed
Summary

Researchers developed a new fluorogenic reaction using inverse electron-demand Diels-Alder chemistry. This method rapidly creates fluorescent dyes directly from nonfluorescent precursors, ideal for bioimaging applications.

Keywords:
bioorthogonal chemistryclick reactionscycloadditionheterocyclesimaging agents

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Area of Science:

  • Organic Chemistry
  • Chemical Biology
  • Materials Science

Background:

  • Fluorogenic reactions are crucial for detecting analytes, but developing new methods remains challenging.
  • Existing fluorogenic reagents often require additional steps or complex structures.

Purpose of the Study:

  • To introduce a novel fluorogenic reaction based on inverse electron-demand Diels-Alder chemistry.
  • To demonstrate the direct formation of fluorescent products from nonfluorescent starting materials.

Main Methods:

  • Utilized inverse electron-demand Diels-Alder reaction between 1,2,4,5-tetrazines and trans-cyclooctene (TCO) isomers.
  • Characterized the resulting fluorescent 1,4-dihydropyridazines using NMR spectroscopy.
  • Employed computational studies to rationalize experimental data.
  • Performed cell-labeling experiments for bioimaging validation.

Main Results:

  • Achieved rapid formation of unprecedented fluorescent 1,4-dihydropyridazines.
  • Demonstrated that the fluorophore is intrinsically formed during the reaction, eliminating the need for external moieties.
  • Showcased tunable photochemical properties by altering tetrazine substitution patterns.
  • Confirmed the utility of the reaction in cell-labeling for bioimaging.

Conclusions:

  • The developed inverse electron-demand Diels-Alder reaction offers a new, efficient strategy for generating fluorescent dyes.
  • This approach simplifies fluorophore synthesis and enables direct, in-situ fluorescence generation.
  • The tunable nature and bioimaging potential highlight its significance in chemical biology and diagnostics.