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Article
Hiroko Yamada
Nara Institute of Science and Technology
Corresponding Author
ORCiD: https://orcid.org/0000-0002-2138-5902
Naoki Aratani
Nara Institute of Science and Technology
Corresponding Author
ORCiD: https://orcid.org/0000-0002-3181-6526
License:
This work is licensed under a CC BY 4.0 License. Read Full License
Optically active fullerenes (C76, C82, C84), including C60 and C70 derivatives carrying organic substituents, possess various potent applications because of unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality has not yet been elucidated because of a very poor quantum yield of fluorescence (FL). With this background in mind, we synthesized new chiral C70 derivatives, X70A, solely by reacting bis-borylated xanthene with C70 in a one-step double addition reaction with 20% yield, followed by a successful optical resolution using a recyclable chiral-HPLC technique. The isolated X70A enantiomers were confirmed by their mirror-image circular dichroism spectra in the range of 300 nm and 700 nm. The enantiomeric pair of X70A in toluene revealed clearly mirror-image circularly polarized luminescence (CPL) spectra with a high |glum| value of 7.0 × 10–3 at 690 nm associated with FL lifetime of 0.99 ns. The deep-red CPL of X70A should provide new photofunctionality as chiral nanocarbon materials.
Keywords
fullerenes, photoexcited chirality, X70A, bis-borylated xanthene, chiral-HPLC, nanocarbon materials
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This is a preprint. It has not completed peer review.
Article
Hiroko Yamada
Nara Institute of Science and Technology
Corresponding Author
ORCiD: https://orcid.org/0000-0002-2138-5902
Naoki Aratani
Nara Institute of Science and Technology
Corresponding Author
ORCiD: https://orcid.org/0000-0002-3181-6526
Badges
Prescreen
This manuscript passed our Prescreen assessment
Complete author information
Appropriate declaration statements
Potential risks to human health
Prescreen
History
CURRENT STATUS: Posted
Version 1
Posted 22 Jul, 2020
No community comments so far
Metrics
Comments: 0
PDF Downloads: ...
HTML Views: ...
License:
This work is licensed under a CC BY 4.0 License. Read Full License
Optically active fullerenes (C76, C82, C84), including C60 and C70 derivatives carrying organic substituents, possess various potent applications because of unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality has not yet been elucidated because of a very poor quantum yield of fluorescence (FL). With this background in mind, we synthesized new chiral C70 derivatives, X70A, solely by reacting bis-borylated xanthene with C70 in a one-step double addition reaction with 20% yield, followed by a successful optical resolution using a recyclable chiral-HPLC technique. The isolated X70A enantiomers were confirmed by their mirror-image circular dichroism spectra in the range of 300 nm and 700 nm. The enantiomeric pair of X70A in toluene revealed clearly mirror-image circularly polarized luminescence (CPL) spectra with a high |glum| value of 7.0 × 10–3 at 690 nm associated with FL lifetime of 0.99 ns. The deep-red CPL of X70A should provide new photofunctionality as chiral nanocarbon materials.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
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