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Related Concept Videos

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

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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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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Determination of the Photoisomerization Quantum Yield of a Hydrazone Photoswitch
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A Photoswitchable Metallocycle Based on Azobenzene: Synthesis, Characterization, and Ultrafast Dynamics.

Raphael I Petrikat1, Justin Hornbogen2, Marcel J P Schmitt1

  • 1Fachbereich Chemie, RPTU Kaiserslautern-Landau, Erwin-Schrödinger-Straße 52-54, 67663, Kaiserslautern, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 25, 2024
PubMed
Summary

Researchers developed the first photoswitchable metal-organic metallocycle using azobenzene. This novel complex exhibits reversible E/Z photoisomerization without degradation, mimicking archetypal azobenzene behavior.

Keywords:
azobenzenecopper metallocyclegas phase transient photodissociationphotoswitchultrafast dynamics

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Area of Science:

  • Supramolecular Chemistry
  • Photochemistry
  • Coordination Chemistry

Background:

  • Azobenzene derivatives are well-known photoswitchable molecules.
  • Development of photoresponsive metal-organic frameworks and metallocycles is an active research area.
  • Understanding photoisomerization dynamics in complex systems is crucial for designing functional materials.

Purpose of the Study:

  • To synthesize and characterize a novel photoswitchable metallocycle based on an azobenzene ligand.
  • To investigate the photoisomerization behavior and dynamics of the metallocycle in solution and gas phase.
  • To elucidate the influence of metal coordination on the azobenzene switching mechanism.

Main Methods:

  • Synthesis of the azobenzene-containing ligand 3,3'-Azobenz(metPA)2 (1) and the copper(I) metallocycle [Cu2(1)2](BF4)2 (2).
  • Characterization using static and time-resolved spectroscopic methods, including femtosecond UV/Vis transient absorption (fs-TA) in solution.
  • Gas-phase transient photodissociation (τ-PD) in a mass spectrometric ion trap.
  • Quantum chemical calculations.

Main Results:

  • The copper(I) metallocycle [Cu2(1)2](BF4)2 (2) was successfully prepared and demonstrated highly quantitative and reproducible photoinduced E/Z switching without complex decay.
  • Ultrafast photoinduced dynamics in the sub-picosecond to few picosecond timescale were observed, consistent with archetypal azobenzene behavior.
  • Gas-phase and solution-phase studies, along with theoretical calculations, revealed that metal coordination has a negligible effect on the switching mechanism and electronic pathway, indicating a non-cooperative isomerization process.

Conclusions:

  • The synthesized [Cu2(1)2](BF4)2 (2) represents the first reversibly photoswitchable (3d)-metallocycle based on azobenzene.
  • The metallocycle exhibits azobenzene-like photoisomerization dynamics, unaffected by metal coordination.
  • The combination of fs-TA and τ-PD provides valuable insights into the interplay of dynamics and solvation in such systems.