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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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.
Valence Bond Theory02:45

Valence Bond Theory

Overview of Valence Bond Theory

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Published on: March 24, 2018

Increasing connectivity through self-complementarity enables permanent porosity in a halogen-bonded organic

Michael P Moghadasnia1, Hayden A Evans2, Adria S Hippely1

  • 1Department of Chemistry, Colorado School of Mines Golden Colorado 80401 USA cmmcguirk@mines.edu.

Chemical Science
|June 25, 2026
PubMed
Summary

Researchers developed the first permanently porous halogen-bonded organic framework (XOF). This new XOF material remains stable after solvent removal, opening new possibilities for porous materials design.

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Crystallography

Background:

  • Halogen bonding is a key interaction for creating ordered molecular solids.
  • Achieving permanent porosity in halogen-bonded materials has been a significant challenge.

Purpose of the Study:

  • To report the first rigorously characterized permanently porous halogen-bonded organic framework (XOF).
  • To demonstrate a self-complementary strategy for creating stable, porous XOFs.

Main Methods:

  • Synthesis of a 2-iodooxazole-terminated tecton.
  • Spontaneous assembly into a crystalline network.
  • Characterization using N2 gas adsorption-desorption at 77 K and X-ray diffraction.

Main Results:

  • The first permanently porous halogen-bonded organic framework (XOF) was successfully synthesized.
  • The XOF exhibited a stable, low-density crystalline network intact after solvent removal.
  • The framework demonstrated 3D connectivity via C-I⋯N halogen bonding and π-stacking.

Conclusions:

  • Halogen bonding can support permanent porosity, overcoming previous limitations.
  • XOFs represent a new class of permanently porous materials with robust intermolecular interactions.
  • This work expands the potential of halogen bonding in advanced materials design.