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Updated: Apr 23, 2026

Interfacial Molecular-level Structures of Polymers and Biomacromolecules Revealed via Sum Frequency Generation Vibrational Spectroscopy
Published on: August 13, 2019
Phosphorus-containing chiral molecule for fullerene recognition based on concave/convex interaction.
Masaki Yamamura1, Tsuyoshi Saito, Tatsuya Nabeshima
1Graduate School of Pure and Applied Sciences and Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), University of Tsukuba , 1-1-1, Tennodai, Tsukuba, Ibaraki 305-8571, Japan.
Researchers synthesized a chiral concave molecule with a central phosphorus atom, resolving its enantiomers. This molecule effectively encapsulated a C60 fullerene, demonstrating its potential as a chiral host for fullerenes.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Chiroptical Spectroscopy
Background:
- Development of novel host molecules for guest encapsulation is crucial in supramolecular chemistry.
- Chiral host molecules offer unique opportunities for enantioselective recognition and separation.
Purpose of the Study:
- To synthesize and characterize a novel C3-symmetric chiral concave molecule containing a central phosphorus atom.
- To investigate the chiroptical properties and host-guest capabilities of the synthesized molecule, particularly with fullerenes.
Main Methods:
- Synthesis of a C3-symmetric chiral concave molecule with a central phosphorus atom.
- Enantiomeric resolution and structural elucidation using X-ray analysis.
- Characterization of chiroptical properties (circular dichroism) and host-guest interactions (NMR, MALDI-TOF mass spectrometry).
Main Results:
- Successful synthesis and enantiomeric resolution of the chiral concave molecule.
- X-ray analysis confirmed the molecule's concave shape and absolute structure.
- The molecule exhibited strong chiroptical properties due to delocalized molecular orbitals.
- Four enantiopure concave molecules were observed to encapsulate a C60 fullerene in a co-crystal structure.
- Evidence of concave/convex interaction between the host molecule and fullerene was obtained.
Conclusions:
- The synthesized phosphorus-containing chiral concave molecule possesses significant chiroptical properties.
- This molecule demonstrates effective host-guest complexation with C60 fullerene.
- The findings highlight the potential of this molecule as a chiral host for fullerenes.
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