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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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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.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
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Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
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Hydrogen-Bond-Network Breakdown Boosts Selective CO2 Photoreduction by Suppressing H2 Evolution.

Die Cong1, Jikai Sun1, Yuwei Pan1

  • 1Institute of Frontier Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Qingdao, 266237, China.

Angewandte Chemie (International Ed. in English)
|March 23, 2024
PubMed
Summary

Breaking hydrogen bonds in photocatalysts suppresses hydrogen gas evolution, significantly boosting carbon dioxide (CO2) photoreduction efficiency and selectivity. This strategy enhances CO2 conversion rates using poly(ionic liquid)s.

Keywords:
hydrogen bond networkphotocatalytic CO2 reductionphotosensitive poly(ionic liquid)suppressing hydrogen evolution

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Area of Science:

  • Materials Science
  • Catalysis
  • Photochemistry

Background:

  • Conventional carbon dioxide (CO2) photoreduction relies heavily on catalyst and cocatalyst design for efficiency and selectivity.
  • Hydrogen (H2) evolution often competes with CO2 reduction, limiting overall performance.
  • Poly(ionic liquid)s exhibit strong hydrogen bonding capabilities with solvents, influencing reaction pathways.

Purpose of the Study:

  • To investigate the impact of hydrogen bond network breakdown on CO2 photoreduction performance.
  • To develop a novel strategy for enhancing CO2 photoreduction by suppressing H2 evolution.
  • To explore the use of photosensitive poly(ionic liquid)s as tunable photocatalysts.

Main Methods:

  • Design and synthesis of photosensitive poly(ionic liquid)s as photocatalysts.
  • Tuning hydrogen bond strength by adjusting solvent composition.
  • Utilizing additives like trichloromethane and tetrachloromethane to induce hydrogen bond network breakdown.
  • Quantifying H2 evolution and CO production rates and selectivity using gas chromatography and Raman spectroscopy.
  • Employing theoretical calculations to confirm the mechanism of hydrogen bond network disruption.

Main Results:

  • Hydrogen bond network breakdown effectively suppressed H2 evolution, with rates reduced to zero in the presence of trichloromethane or tetrachloromethane.
  • CO production rate increased significantly to 35.4 mmol g⁻¹ h⁻¹ with trichloromethane, a substantial improvement from 0.6 mmol g⁻¹ h⁻¹ without additives.
  • CO selectivity reached 98.9% with trichloromethane, compared to 26.2% without additives, demonstrating enhanced CO2 photoreduction performance.

Conclusions:

  • Disrupting the hydrogen bond network is a viable strategy to suppress competing H2 evolution in photocatalytic systems.
  • Photosensitive poly(ionic liquid)s offer tunable properties for controlling hydrogen bonding and optimizing CO2 photoreduction.
  • The developed hydrogen bond network breakdown strategy shows potential for broader application in catalytic reactions involving H2 evolution.