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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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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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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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.
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Expression and Purification of Nuclease-Free Oxygen Scavenger Protocatechuate 3,4-Dioxygenase
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Supramolecular Control of Singlet Oxygen Generation.

Akshay Kashyap1, Elamparuthi Ramasamy2, Vijayakumar Ramalingam3

  • 1Department of Chemistry, University of Nebraska Kearney, Kearney, NE 68849, USA.

Molecules (Basel, Switzerland)
|June 2, 2021
PubMed
Summary

Supramolecular photochemistry enhances singlet oxygen generation (SOG) by controlling photosensitizer structure. This approach unlocks new technological potential for SOG applications in medicine and chemistry.

Keywords:
calixarenecavitandscucurbiturilcyclodextrinnear IR (NIR)oxidationphotodynamic therapy (PDT)photosensitizer (PS)singlet oxygensinglet oxygen generation (SOG)supramolecular chemistry

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Area of Science:

  • Photochemistry
  • Supramolecular Chemistry
  • Physical Chemistry

Background:

  • Singlet oxygen (1O2) is a reactive oxygen species produced via photosensitized excitation.
  • Photochemical singlet oxygen generation (SOG) has diverse applications in medicine, environmental remediation, and synthesis.
  • Historically, photosensitizer (PS) design focused on intrinsic structure and energetics.

Purpose of the Study:

  • To review the progress of singlet oxygen generation (SOG) using supramolecular photochemistry.
  • To highlight the supramolecular approach for designing efficient photosensitizers.
  • To serve as a reference for future research in SOG.

Main Methods:

  • Review of existing literature on supramolecular photochemistry and SOG.
  • Analysis of how non-bonding interactions influence photosensitizer performance.
  • Compilation of advancements in SOG through supramolecular strategies.

Main Results:

  • Supramolecular strategies enable the use of previously inactive or less effective photosensitizers for SOG.
  • Non-bonding interactions offer precise control over photosensitizer structure and energetics.
  • This approach significantly enhances the efficiency of singlet oxygen generation.

Conclusions:

  • Supramolecular photochemistry provides a powerful platform for optimizing singlet oxygen generation.
  • This review underscores the untapped technological potential of SOG via supramolecular design.
  • Future research can leverage supramolecular principles to advance SOG applications.