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Related Concept Videos

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...
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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.
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.
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy between bonds broken and bonds...
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.

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Related Experiment Video

Updated: May 22, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

Halogen-Rich Design Strategy: Rational Synthesis of High-Performance Tetrahedron-Based Chalcohalides for Advanced

Wen-Li Zhao1, Rui-Xi Wang1, Shuang Zhao2

  • 1College of Chemistry, Beijing Normal University, Beijing, People's Republic of China.

Angewandte Chemie (International Ed. in English)
|May 21, 2026
PubMed
Summary

Researchers developed novel halogen-rich chalcohalides, overcoming synthetic challenges to unlock superior nonlinear optical properties. These new materials offer enhanced performance for advanced optical applications.

Keywords:
chalcohalidehalogen‐richheteroligand [MCh4‐xXx] moietiesinfrared nonlinear optical crystalssecond harmonic generation

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Published on: September 8, 2017

Area of Science:

  • Materials Science
  • Solid-State Chemistry
  • Nonlinear Optics

Background:

  • Anisotropic structure building units with diverse chemical bonds (ABUCB) concept suggests tetrahedron-based chalcohalides offer superior nonlinear optical (NLO) performance.
  • Existing chalcohalides predominantly feature chalcogen-rich (Ch-rich) compositions, limiting exploration of halogen-rich (X-rich) structures.
  • The underutilization of X-rich chalcohalides is attributed to thermodynamic and stoichiometric synthetic constraints, not inherent instability.

Purpose of the Study:

  • To overcome the synthetic limitations hindering the development of X-rich chalcohalides.
  • To explore the NLO potential of novel X-rich chalcohalide compounds.
  • To identify materials with enhanced NLO properties, wide band gaps, and broad IR transparency.

Main Methods:

  • Development of an X-rich design strategy to circumvent thermodynamic and stoichiometric synthetic traps.
  • Synthesis and characterization of novel A4Ga4Se2X12, A4M4Se3Cl10, Cs4Ga4Se4Cl8, and Cs3Al6Se10Cl compounds.
  • Evaluation of NLO properties, including second-harmonic generation (SHG) response, band gap, laser-induced damage threshold (LIDT), birefringence, and IR transparency.

Main Results:

  • Successful synthesis of the first series of X-rich chalcohalides, including A4Ga4Se2X12 (X=Cl, Br) and A4M4Se3Cl10 (M=Ga, Al).
  • The noncentrosymmetric compound Cs4Ga4Se4Cl8 (4) exhibits exceptional NLO performance: 4.27 × AgGaS2 SHG response, 4.05 eV band gap, 50 × AgGaS2 LIDT, and phase-matching compatible birefringence.
  • Compound 4 demonstrates the broadest IR transparency window among NLO chalcohalides, extending from 0.26 to 25 µm.

Conclusions:

  • The developed X-rich design strategy effectively overcomes synthetic barriers, enabling access to previously unexplored chalcohalide compositions.
  • The novel X-rich chalcohalides, particularly Cs4Ga4Se4Cl8, possess outstanding NLO properties suitable for advanced photonic applications.
  • These findings open new avenues for designing high-performance NLO materials with tailored properties and broad spectral windows.