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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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: 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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Cycloaddition Reactions: MO Requirements for Thermal Activation

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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.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.2K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst
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Photocontrolled On-Surface Pseudorotaxane Formation with Well-Ordered Macrocycle Multilayers.

Felix B Schwarz1, Thomas Heinrich1,2, J Ole Kaufmann1

  • 1Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 20, 2016
PubMed
Summary

Researchers explored photoinduced pseudorotaxane formation using a novel photoswitchable unit and macrocycles. This study demonstrates photocontrolled assembly on functionalized glass surfaces, enhancing molecular order.

Keywords:
azobenzenephotochemistrypseudorotaxanessupramolecular chemistrysurface chemistry

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Photochemistry

Background:

  • Photoresponsive materials enable dynamic control over molecular assembly.
  • Macrocycles can form inclusion complexes with suitable guest molecules.
  • Surface immobilization allows for the development of functional materials and devices.

Purpose of the Study:

  • To investigate the photoinduced pseudorotaxane formation between a photoresponsive axle and tetralactam macrocycles.
  • To synthesize and characterize a novel photoswitchable binding station.
  • To explore the immobilization of macrocycles on glass surfaces and photocontrolled guest binding.

Main Methods:

  • Synthesis of a novel photoswitchable binding station containing azobenzene and diketopiperazine.
  • Solution-phase and surface-based studies using NMR and UV/Vis spectroscopy.
  • Functionalization of glass surfaces with self-assembled monolayers (SAMs) and layer-by-layer assembly of macrocycles.
  • Characterization of surface-bound macrocycles using NEXAFS spectroscopy.

Main Results:

  • Successful synthesis and characterization of a novel photoswitchable binding station.
  • Demonstration of photoinduced pseudorotaxane formation in solution and on immobilized macrocycle multilayers.
  • Confirmation of preferred macrocycle orientation on functionalized surfaces via NEXAFS.
  • Observation of photocontrolled deposition of the axle into surface-bound macrocycles, leading to increased molecular order.

Conclusions:

  • Photoinduced pseudorotaxane formation is achievable with novel photoswitchable units and surface-immobilized macrocycles.
  • Surface functionalization and layer-by-layer assembly enable controlled immobilization of macrocycles with preferred orientation.
  • Photocontrolled guest binding on surfaces enhances molecular order, paving the way for light-responsive materials.