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Related Concept Videos

Prochirality02:05

Prochirality

3.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.2K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.2K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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...
5.8K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.9K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
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Arene-Perfluoroarene Force Driven Sublimation-Removable Chiral Coassemblies.

Bingyu Liu1, Junjie Gao1, Aiyou Hao1

  • 1Key Laboratory of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.

Angewandte Chemie (International Ed. in English)
|April 24, 2023
PubMed
Summary

We developed a novel chiral coassembly using a sacrificial template that allows for tunable supramolecular chirality and circularly polarized luminescence (CPL). This method enables the removal of the template, retaining desired chiroptical properties for advanced materials.

Keywords:
Arene-Perfluoroarene InteractionChiral Self-AssemblyCircularly Polarized LuminescenceSacrificial Template MethodSublimation

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

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Chiroptical Spectroscopy

Background:

  • Multiple constituent coassembly is key for controlling supramolecular chirality and chiroptical properties like circularly polarized luminescence (CPL).
  • Existing methods struggle to remove secondary or tertiary components after initial self-assembly, limiting tunability.

Purpose of the Study:

  • To develop a novel, constitute-removable chiral coassembly system.
  • To achieve tunable supramolecular chirality, luminescence, and CPL properties.
  • To demonstrate a green and efficient method for creating advanced chiroptical materials.

Main Methods:

  • Coassembly of octafluoronaphthalene (OFN) with perylene-conjugated peptoids via arene-perfluoroarene (AP) interactions.
  • Utilizing OFN as a sacrificial template due to its low sublimation enthalpy.
  • Employing vacuum-treatment to remove OFN via sublimation, followed by characterization using X-ray diffraction and chiroptical spectroscopy.

Main Results:

  • OFN coassembly induced macroscopic chirality and hypsochromic luminescence shifts (yellow to green).
  • OFN accelerated 1D growth, leading to emergent chirality and CPL.
  • Sacrificial removal of OFN via sublimation retained helical nanoarchitectures and chiroptical activity (Cotton effects and CPL).
  • X-ray diffraction indicated molecular void consolidation after OFN removal, with minor alterations to molecular arrangements.

Conclusions:

  • A constitute-removable chiral coassembly strategy using sublimation was successfully developed.
  • This method allows for tunable chiroptical properties and the creation of stable helical nanoarchitectures.
  • The sacrificial sublimation approach is a green, efficient, and non-destructive technique applicable to template-directed chiroptical materials and devices.