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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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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.
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Synthesis, Structures, and CPL Property of Inner-Wall Modified Pagoda[5]Arenes Driven by Cavity Microenvironment.

Yu-Jie Long1,2, Wei-Chen Guo1,2, Jun-Feng Xiang1

  • 1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.

Angewandte Chemie (International Ed. in English)
|October 1, 2025
PubMed
Summary

Researchers developed a novel inner-wall modification strategy for pagoda[5]arene (P5) to achieve fixed conformation and stable chirality. This method enables efficient synthesis of chiral macrocyclic arenes for supramolecular chemistry applications.

Keywords:
ChiralityCircularly polarized luminescenceConformationDiels–Alder cycloadditionMacrocyclic arenes

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Macrocyclic arenes with large cavities and chirality are valuable in supramolecular chemistry.
  • Achieving fixed conformation and stable chirality in these molecules presents significant challenges.
  • Existing rim functionalization methods often suffer from poor selectivity and efficiency.

Purpose of the Study:

  • To develop a novel strategy for fixing the conformation and achieving stable chirality of pagoda[5]arene (P5) through inner-wall modification.
  • To explore the efficiency and selectivity of Diels-Alder (D-A) cycloadditions for inner-wall functionalization.
  • To investigate the chiral properties of the resulting modified macrocyclic arenes.

Main Methods:

  • Developed an inner-wall modification strategy for P5 using Diels-Alder (D-A) cycloadditions.
  • Utilized pre-organized guest molecules within the P5 cavity to direct the cycloaddition reaction.
  • Synthesized a series of inner-wall modified P5 derivatives under mild conditions.
  • Obtained a neutral derivative (P5py) via post-reaction demethylation and resolved its enantiomers using chiral High-Performance Liquid Chromatography (HPLC).

Main Results:

  • Achieved high yields and selectivity in the D-A cycloadditions for inner-wall modification of P5.
  • Demonstrated that the cavity microenvironment of P5 is crucial for the reaction, as control experiments without it showed no reaction.
  • The neutral P5py derivative exhibited stable planar chirality, with resolved enantiomers showing mirror-imaged Circular Dichroism (CD) signals and strong Circularly Polarized Luminescence (CPL) properties.

Conclusions:

  • The developed inner-wall modification strategy provides a facile and efficient route to fixed-conformation, chiral macrocyclic arenes.
  • This approach overcomes limitations of traditional rim functionalization methods.
  • The study broadens the prospects for macrocyclic arenes in supramolecular chemistry and materials science due to their tunable chiral properties.