Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment

A fully conjugated azacorannulene dimer with a large π-surface (76π system) was successfully synthesized from a fully conjugated bifunctional polycyclic aromatic azomethine ylide. This molecule represents an example of diaza[80]fullerene (C78N2) fragment molecule bearing two internal nitrogen atoms....

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Main Authors:	Wang, Weifan, Hanindita, Fiona, Hamamoto, Yosuke, Li, Yongxin, Ito, Shingo
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2022
Subjects:	Science::Chemistry Chemical Compound Annulene Derivative
Online Access:	https://hdl.handle.net/10356/160406
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Institution:	Nanyang Technological University
Language:	English

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spelling	sg-ntu-dr.10356-1604062023-02-28T20:00:49Z Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment Wang, Weifan Hanindita, Fiona Hamamoto, Yosuke Li, Yongxin Ito, Shingo School of Physical and Mathematical Sciences Science::Chemistry Chemical Compound Annulene Derivative A fully conjugated azacorannulene dimer with a large π-surface (76π system) was successfully synthesized from a fully conjugated bifunctional polycyclic aromatic azomethine ylide. This molecule represents an example of diaza[80]fullerene (C78N2) fragment molecule bearing two internal nitrogen atoms. X-ray crystallography analysis shows its boat-shaped structure with two terminal azacorannulenes bent in the same direction. The molecular shape leads to unique selective association with a dumbbell-shaped C60 dimer (C120) over C60 through shape recognition. Owing to its large π-surface and a narrow HOMO-LUMO gap, the azacorannulene dimer exhibits red fluorescence with a quantum yield of up to 31%. The utilization of the fully conjugated bifunctional azomethine ylide is a powerful method for the bottom-up synthesis of large multiazafullerene fragments, providing a step towards the selective total synthesis of multiazafullerenes. Published version 2022-07-21T05:15:25Z 2022-07-21T05:15:25Z 2022 Journal Article Wang, W., Hanindita, F., Hamamoto, Y., Li, Y. & Ito, S. (2022). Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment. Nature Communications, 13(1), 1498-. https://dx.doi.org/10.1038/s41467-022-29106-w 2041-1723 https://hdl.handle.net/10356/160406 10.1038/s41467-022-29106-w 35314682 2-s2.0-85126755729 1 13 1498 en Nature Communications © 2022 The Author(s). 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 license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license 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 license, visit http://creativecommons.org/ licenses/by/4.0/. application/pdf
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	Science::Chemistry Chemical Compound Annulene Derivative
spellingShingle	Science::Chemistry Chemical Compound Annulene Derivative Wang, Weifan Hanindita, Fiona Hamamoto, Yosuke Li, Yongxin Ito, Shingo Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
description	A fully conjugated azacorannulene dimer with a large π-surface (76π system) was successfully synthesized from a fully conjugated bifunctional polycyclic aromatic azomethine ylide. This molecule represents an example of diaza[80]fullerene (C78N2) fragment molecule bearing two internal nitrogen atoms. X-ray crystallography analysis shows its boat-shaped structure with two terminal azacorannulenes bent in the same direction. The molecular shape leads to unique selective association with a dumbbell-shaped C60 dimer (C120) over C60 through shape recognition. Owing to its large π-surface and a narrow HOMO-LUMO gap, the azacorannulene dimer exhibits red fluorescence with a quantum yield of up to 31%. The utilization of the fully conjugated bifunctional azomethine ylide is a powerful method for the bottom-up synthesis of large multiazafullerene fragments, providing a step towards the selective total synthesis of multiazafullerenes.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Wang, Weifan Hanindita, Fiona Hamamoto, Yosuke Li, Yongxin Ito, Shingo
format	Article
author	Wang, Weifan Hanindita, Fiona Hamamoto, Yosuke Li, Yongxin Ito, Shingo
author_sort	Wang, Weifan
title	Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
title_short	Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
title_full	Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
title_fullStr	Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
title_full_unstemmed	Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
title_sort	fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment
publishDate	2022
url	https://hdl.handle.net/10356/160406
_version_	1759853556667514880

Fully conjugated azacorannulene dimer as large diaza[80]fullerene fragment

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