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Related Concept Videos

Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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.
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.

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Related Experiment Video

Updated: Jun 11, 2026

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

Halogenation engineered metal cluster assemblies.

Xiao-Yan Shi1, Xing-Nan Wang1, Li-Xia Huang1

  • 1Key Laboratory of Special Functional Molecular Materials (Zhengzhou University), Ministry of Education, Henan Key Laboratory of Crystalline Molecular Functional Materials, College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.

National Science Review
|June 10, 2026
PubMed
Summary
This summary is machine-generated.

We developed a halogenation strategy for gold clusters, enabling precise control over self-assembly into diverse chiral nanomaterials with tunable optical properties.

Keywords:
circularly polarized luminescencecoinage metal clustershalogenation engineeringself-assemblysupramolecular chirality

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Synthesis of a Water-soluble Metal&#8211;Organic Complex Array
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Synthesis of a Water-soluble Metal–Organic Complex Array

Published on: October 8, 2016

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Last Updated: Jun 11, 2026

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Synthesis of a Water-soluble Metal&#8211;Organic Complex Array
06:40

Synthesis of a Water-soluble Metal–Organic Complex Array

Published on: October 8, 2016

Area of Science:

  • Supramolecular Chemistry
  • Materials Chemistry
  • Nanomaterials Science

Background:

  • Achieving predictable macroscopic functions from molecular design is a key goal in supramolecular and materials chemistry.
  • Atomically precise coinage metal clusters are promising for this, but assembly control, especially for chirality transfer, is limited.
  • Conventional noncovalent interactions in metal clusters offer poor tunability for complex assembly.

Purpose of the Study:

  • To introduce a halogenation engineering strategy for tunable, directional noncovalent interactions in gold clusters.
  • To demonstrate control over self-assembly into multiple, structurally distinct polymorphs from a single precursor.
  • To achieve efficient transfer and amplification of molecular chirality to the supramolecular level, yielding advanced chiral nanomaterials.

Main Methods:

  • Selective installation of distinct halogens (F, Cl, Br) on peripheral ligands of tetranuclear gold clusters.
  • Utilizing directional noncovalent interactions (hydrogen bonding, halogen bonding, halogen···halogen) to direct assembly.
  • Modulating the external solvent environment to bias interactions and control polymorph formation.

Main Results:

  • Demonstrated rational control over self-assembly into discrete monomers, helices, and chains from a single gold cluster precursor.
  • Achieved efficient preservation, transfer, and amplification of molecular chirality into supramolecular structures.
  • Reported intense circularly polarized luminescence in a gold cluster trimer with high quantum yield (94%) and dissymmetry factor (g_lum = 0.04).

Conclusions:

  • Established clear design principles for directing cluster self-assembly via peripheral atom substitution.
  • Developed a rational methodology for the bottom-up fabrication of advanced chiral nanomaterials.
  • Showcased the potential of halogenation engineering to overcome limitations in supramolecular assembly and create functional nanomaterials.