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Related Concept Videos

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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.
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:
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...

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Related Experiment Video

Updated: Jul 14, 2026

Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films
08:12

Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films

Published on: September 8, 2017

Cation-dominated second-harmonic generation in chiral tetrahydro-1-naphthylammonium halides.

Youpei Zhang1, Junjie Guan1, Jing Zhang1

  • 1School of Materials Science and Engineering, Tianjin Key Laboratory of Metal and Molecular Materials Chemistry, Frontiers Science Center for New Organic Matter, Academy for Advanced Interdisciplinary Studies, Nankai University, Tianjin 300350, P. R. China. yangyimin@nankai.edu.cn.

Dalton Transactions (Cambridge, England : 2003)
|July 13, 2026
PubMed
Summary

We developed new nonlinear optical (NLO) materials using chiral organic cations, specifically R-/S-1,2,3,4-tetrahydro-1-naphthylamine (R-/S-THNA), to achieve significant second-harmonic generation (SHG) effects.

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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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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

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Last Updated: Jul 14, 2026

Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films
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Low Pressure Vapor-assisted Solution Process for Tunable Band Gap Pinhole-free Methylammonium Lead Halide Perovskite Films

Published on: September 8, 2017

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

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Area of Science:

  • Materials Science
  • Optoelectronics
  • Crystallography

Background:

  • Nonlinear optical (NLO) materials are crucial for optoelectronic devices and medical imaging.
  • Traditional NLO material design often overlooks the contribution of cations, focusing primarily on anionic groups.
  • Chiral organic cations offer a potential avenue for novel NLO properties.

Purpose of the Study:

  • To investigate the NLO properties of materials where chiral organic cations dominate the second-order nonlinear optical response.
  • To explore the synthesis and characterization of new NLO materials based on chiral ammonium halides.
  • To challenge the traditional anionic group theory in NLO material design.

Main Methods:

  • Synthesis of enantiomeric pairs of R-/S-THNA·HCl and R-/S-THNA·HBr using enantiopure R-/S-1,2,3,4-tetrahydro-1-naphthylamine (R-/S-THNA).
  • Growth of high-quality, centimeter-sized single crystals.
  • Crystallographic analysis to determine space groups and structural properties.
  • Evaluation of second-harmonic generation (SHG) effects and thermal stability.

Main Results:

  • Successfully synthesized R-/S-THNA·HCl and R-/S-THNA·HBr with excellent thermal stability and UV transparency.
  • Crystals were obtained in non-centrosymmetric space groups, confirming their potential for SHG.
  • The observed SHG effects were predominantly attributed to the chiral R-/S-THNA+ cations, not the halide anions.
  • Both R- and S-THNA+ cations exhibited similar first hyperpolarizabilities, indicating chirality's role in NLO response.

Conclusions:

  • Chiral organic cations can be the primary source of significant second-harmonic generation (SHG) effects in NLO materials.
  • This cation-dominated strategy offers a new paradigm for designing NLO materials, moving beyond traditional anionic group focus.
  • The developed R-/S-THNA·HCl and R-/S-THNA·HBr serve as promising candidates for optoelectronic applications.