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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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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Dynamic Covalent Platform for Chiroptically Tunable Figure-Eight Macrocycles from Preorganized Alkaloidal Scaffolds.

Shunsuke Murakami1, Tasuku Honda1, Takashi Fushiki1

  • 1Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku 113-0033, Tokyo, Japan.

JACS Au
|February 27, 2026
PubMed
Summary

Researchers developed a dynamic covalent platform to create tunable chiral figure-eight macrocycles from a natural product-inspired scaffold. This method allows for precise control over chiroptical properties in advanced materials.

Keywords:
chiroptically tunable emitterscircular polarized luminescencedynamic covalent chemistryfigure-eight topologymodular macrocycle synthesispreorganized alkaloidal scaffolds

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Area of Science:

  • Supramolecular Chemistry
  • Organic Materials Science
  • Chiroptical Materials

Background:

  • Chiral D2-symmetric figure-eight macrocycles with extended π-conjugated systems are key scaffolds for advanced chiroptical materials.
  • Developing efficient and tunable synthetic routes to these complex structures remains a challenge.

Purpose of the Study:

  • To establish a dynamic covalent platform for synthesizing tunable chiral figure-eight macrocycles.
  • To explore the relationship between molecular architecture and chiroptical properties.
  • To translate natural-product-inspired scaffolds into functional materials.

Main Methods:

  • Utilized a preorganized alkaloidal bispyrrolidinoindoline (BPI) scaffold.
  • Employed thermodynamically controlled imine formation for macrocyclization.
  • Incorporated aryl-ethynyl substituents for scaffold preorganization and chromophore diversity.
  • Performed postsynthetic conversion of imine linkages to rigid B-N chelates via boranil formation.

Main Results:

  • Achieved highly efficient macrocyclization (up to 81% yield) using reversible imine chemistry.
  • Synthesized 44-90 membered macrocycles with predictable optical and chiroptical responses.
  • Generated a bright orange emitter with high fluorescence quantum yield (Φfl = 0.54).
  • Observed enhanced circularly polarized luminescence (CPL) activity (glum = 1.97 × 10⁻³).

Conclusions:

  • Established a general design principle integrating dynamic covalent chemistry and conformational preorganization.
  • Demonstrated a modular approach for creating diverse, tunable chiroptical materials.
  • Successfully translated natural-product-inspired molecular architecture into functional figure-eight macrocycles.