Deep-red circularly polarised luminescent C(70) derivatives

Optically active fullerenes, including C(60) and C(70) derivatives carrying organic substituents, are used in a range of applications because of their unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality is yet to be elucidated because of...

Descripción completa

Detalles Bibliográficos
Autores principales: Kano, Haruka, Hayashi, Hironobu, Matsuo, Kyohei, Fujiki, Michiya, Yamada, Hiroko, Aratani, Naoki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8187662/
https://www.ncbi.nlm.nih.gov/pubmed/34103595
http://dx.doi.org/10.1038/s41598-021-91451-5
_version_ 1783705177671335936
author Kano, Haruka
Hayashi, Hironobu
Matsuo, Kyohei
Fujiki, Michiya
Yamada, Hiroko
Aratani, Naoki
author_facet Kano, Haruka
Hayashi, Hironobu
Matsuo, Kyohei
Fujiki, Michiya
Yamada, Hiroko
Aratani, Naoki
author_sort Kano, Haruka
collection PubMed
description Optically active fullerenes, including C(60) and C(70) derivatives carrying organic substituents, are used in a range of applications because of their unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality is yet to be elucidated because of their very poor fluorescence quantum yield (Φ(f)). We synthesised a new chiral C(70) derivative, X70A, with 20% yield, by reacting bis-borylated xanthene with C(70) in a one-step double addition reaction, followed by a successful optical resolution. The isolation of two separate X70A enantiomers was confirmed by mirror-image circular dichroism spectroscopy in the range of 300–750 nm. In toluene, the enantiomeric pair of X70A clearly revealed mirror-image circularly polarised luminescence (CPL) spectra with a high |g(lum)| value of 7.0 ×  10(−3) at 690 nm. The first fullerene-based deep-red CPL of X70A should provide a new guideline for the design of chiral nanocarbon materials.
format Online
Article
Text
id pubmed-8187662
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-81876622021-06-09 Deep-red circularly polarised luminescent C(70) derivatives Kano, Haruka Hayashi, Hironobu Matsuo, Kyohei Fujiki, Michiya Yamada, Hiroko Aratani, Naoki Sci Rep Article Optically active fullerenes, including C(60) and C(70) derivatives carrying organic substituents, are used in a range of applications because of their unique spectroscopic, catalytic, and chiral recognition properties. However, their inherent photoexcited chirality is yet to be elucidated because of their very poor fluorescence quantum yield (Φ(f)). We synthesised a new chiral C(70) derivative, X70A, with 20% yield, by reacting bis-borylated xanthene with C(70) in a one-step double addition reaction, followed by a successful optical resolution. The isolation of two separate X70A enantiomers was confirmed by mirror-image circular dichroism spectroscopy in the range of 300–750 nm. In toluene, the enantiomeric pair of X70A clearly revealed mirror-image circularly polarised luminescence (CPL) spectra with a high |g(lum)| value of 7.0 ×  10(−3) at 690 nm. The first fullerene-based deep-red CPL of X70A should provide a new guideline for the design of chiral nanocarbon materials. Nature Publishing Group UK 2021-06-08 /pmc/articles/PMC8187662/ /pubmed/34103595 http://dx.doi.org/10.1038/s41598-021-91451-5 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Kano, Haruka
Hayashi, Hironobu
Matsuo, Kyohei
Fujiki, Michiya
Yamada, Hiroko
Aratani, Naoki
Deep-red circularly polarised luminescent C(70) derivatives
title Deep-red circularly polarised luminescent C(70) derivatives
title_full Deep-red circularly polarised luminescent C(70) derivatives
title_fullStr Deep-red circularly polarised luminescent C(70) derivatives
title_full_unstemmed Deep-red circularly polarised luminescent C(70) derivatives
title_short Deep-red circularly polarised luminescent C(70) derivatives
title_sort deep-red circularly polarised luminescent c(70) derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8187662/
https://www.ncbi.nlm.nih.gov/pubmed/34103595
http://dx.doi.org/10.1038/s41598-021-91451-5
work_keys_str_mv AT kanoharuka deepredcircularlypolarisedluminescentc70derivatives
AT hayashihironobu deepredcircularlypolarisedluminescentc70derivatives
AT matsuokyohei deepredcircularlypolarisedluminescentc70derivatives
AT fujikimichiya deepredcircularlypolarisedluminescentc70derivatives
AT yamadahiroko deepredcircularlypolarisedluminescentc70derivatives
AT arataninaoki deepredcircularlypolarisedluminescentc70derivatives

Ejemplares similares