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Prochirality02:05

Prochirality

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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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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.
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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.
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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A Precisely Bromo-Functionalized [9]Cycloparaphenylene as a Platform for Late-Stage Multisite π-Extension Toward

Naoya Kinoshita1, Nanami Kotani1, Masaya Sugiura1

  • 1Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.

Angewandte Chemie (International Ed. in English)
|December 31, 2025
PubMed
Summary

Researchers synthesized a novel [9]cycloparaphenylene ([9]CPP) derivative with precisely placed bromo groups. This functionalized nanohoop exhibits phosphorescence and exceptional chiroptical properties after π-extension.

Keywords:
Au(I) ComplexCircularly Polarized Luminescence (CPL)CycloparaphenylenePhosphorescenceπ‐Extension

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Selective functionalization of [n]cycloparaphenylenes ([n]CPPs) is synthetically challenging due to ring strain.
  • Developing methods for controlled substitution on CPPs is crucial for tailoring their properties.

Purpose of the Study:

  • To synthesize a [9]CPP derivative with orderly introduced bromo groups.
  • To explore the photophysical properties and further functionalization potential of the bromo-substituted [9]CPP.

Main Methods:

  • Utilized an Au-mediated synthetic strategy for efficient [9]CPP construction.
  • Employed Pd-catalyzed coupling reactions for post-functionalization and π-extension.

Main Results:

  • Achieved scalable synthesis of a [9]CPP derivative with bromo groups at specific positions in five steps (37% yield).
  • Observed low-temperature phosphorescence attributed to the heavy-atom effect of bromine.
  • Created a chiral nanohoop via multisite π-extension with significant chiroptical performance (|glum| = 0.100).

Conclusions:

  • Demonstrated a viable route for selective functionalization of [9]CPPs.
  • Highlighted the potential of bromo-substituted CPPs as platforms for advanced materials with tunable photophysical and chiroptical properties.