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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: 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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.1K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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.
18.4K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.3K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.3K

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Azobenzene-Functionalized UiO-66-NH2: Solid Base Catalysts with Photocontrollable Activity.

Hui Wen1, Wen-Juan Zhang1, Ze-Jiu Diao1

  • 1State Key Laboratory of Materials-Oriented Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, College of Chemistry and Chemical Engineering, Nanjing Tech University, Nanjing 211816, China.

Inorganic Chemistry
|May 24, 2023
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Summary
This summary is machine-generated.

Researchers developed a novel smart solid base catalyst using photoresponsive azobenzene derivatives. This catalyst

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Area of Science:

  • Materials Science
  • Catalysis
  • Photochemistry

Background:

  • Heterogeneous solid base catalysts offer high activity and environmental benefits.
  • Traditional catalysts' activity is limited by external factors like temperature and pressure.
  • In situ regulation of catalyst properties for activity control is an emerging area.

Purpose of the Study:

  • To design and synthesize a novel smart solid base catalyst.
  • To enable remote control of catalytic activity using light.
  • To investigate light-induced property changes for activity modulation.

Main Methods:

  • Chemically anchoring photoresponsive azobenzene (p-phenylazobenzoyl chloride, PAC) onto UiO-66-NH2 (UN) metal-organic framework.
  • Utilizing UV and visible light irradiation to induce trans/cis isomerization of PAC.
  • Evaluating catalytic activity in Knoevenagel condensation reactions.

Main Results:

  • The prepared smart catalyst exhibits regular crystal structure and photoresponsive properties.
  • Light irradiation induced significant isomerization of PAC, leading to tunable catalytic activity.
  • A 56.2% change in catalytic activity was observed in Knoevenagel condensation, attributed to steric hindrance changes.

Conclusions:

  • A novel photoresponsive solid base catalyst was successfully developed.
  • Catalytic activity can be precisely regulated by external light through molecular isomerization.
  • This approach offers a new paradigm for designing smart catalysts with tailorable properties.