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Deep-red circularly polarised luminescent C70 derivatives
Haruka Kano1, Hironobu Hayashi1, Kyohei Matsuo1
1Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama-cho, Ikoma, Nara, 630-0192, Japan.
Scientific Reports
|June 9, 2021
Summary
Researchers developed a new chiral fullerene C70 derivative, X70A, enabling the study of photoexcited chirality. This optically active fullerene exhibits strong circularly polarized luminescence, paving the way for novel chiral nanocarbon materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Spectroscopy
Background:
- Optically active fullerenes (C60 and C70 derivatives) possess unique properties valuable in various applications.
- Their photoexcited chirality remains poorly understood due to low fluorescence quantum yields (Φf).
Purpose of the Study:
- To synthesize and characterize a novel chiral C70 derivative to investigate photoexcited chirality.
- To explore the circularly polarized luminescence (CPL) properties of this new fullerene.
Main Methods:
- One-step double addition reaction between bis-borylated xanthene and C70 to synthesize the X70A derivative.
- Optical resolution to isolate individual enantiomers.
- Circular dichroism (CD) spectroscopy to confirm enantiomeric separation.
- Measurement of circularly polarized luminescence (CPL) spectra.
Main Results:
- Successful synthesis of a new chiral C70 derivative (X70A) with a 20% yield.
- Confirmation of two isolated X70A enantiomers using mirror-image CD spectra (300-750 nm).
- Observation of mirror-image CPL spectra for the X70A enantiomeric pair in toluene, with a high luminescence dissymmetry factor (|glum| = 7.0 × 10−3 at 690 nm).
Conclusions:
- The synthesized X70A derivative exhibits the first deep-red CPL from a fullerene.
- This finding offers a new direction for designing chiral nanocarbon materials with tailored optical properties.
