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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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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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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Photoregulated Supramolecular Polymerization through Halogen Bonding.

Alejandro Martínez Manjarres1, Antonia Albers1, Gustavo Fernández1

  • 1Universität Münster, Organisch-Chemisches Institut, Corrensstraße 36, 48149, Münster, Germany.

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Summary

Researchers developed adaptive supramolecular polymers using halogen bonding (XB). These polymers exhibit controlled photoresponsive and adaptive behaviors, offering new possibilities for advanced materials.

Keywords:
aqueous self-assemblyhalogen bondingphotoresponsive systemssupramolecular polymerizationπ-conjugated systems

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Polymer Chemistry

Background:

  • Supramolecular polymers exhibit stimuli-responsive properties, but independent control of these responses remains a challenge.
  • Halogen bonding (XB) is explored as a dynamic network element for regulating material behavior.

Purpose of the Study:

  • To investigate the use of halogen bonding (XB) in creating photoresponsive and adaptive supramolecular polymers.
  • To design and synthesize a two-component system for controlled self-assembly and stimuli-response.

Main Methods:

  • Design of an amphiphilic XB acceptor (OPE-Py) and a photoresponsive XB donor [(E)-Azo-I].
  • Self-assembly studies in aqueous media to form supramolecular polymers, nanoparticles, and 2D sheets.
  • Investigation of stimuli-induced transformations (photoirradiation, heating) and reversibility.

Main Results:

  • OPE-Py self-assembles into polymers, forming nanoparticle assemblies with (E)-Azo-I.
  • Photoirradiation in the presence of (E)-Azo-I leads to the formation of 2D sheet assemblies.
  • Heating dissociates XB interactions, reverting assemblies to the original fiber-like morphology, demonstrating a programmable reset.

Conclusions:

  • Halogen bonding (XB) effectively regulates photoresponsive and adaptive behaviors in supramolecular polymers.
  • The developed system allows for distinct stimuli-responses and a programmable reset mechanism.
  • This work expands the application of XB in solution assemblies and enables multifunctional adaptive materials.