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Synthesis of metalla-dual-azulenes with fluoride ion recognition properties
Azulene-based conjugated systems are of great interests due to their unusual structures and photophysical properties. Incorporation of a transition metal into azulene skeleton presents an intriguing opportunity to combine the d(π)-p(π) and p(π)-p(π) conjugated properties. No such metallaazulene skel...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10495402/ https://www.ncbi.nlm.nih.gov/pubmed/37696902 http://dx.doi.org/10.1038/s41467-023-41250-5 |
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author | Liu, Hai-Cheng Ruan, Kaidong Ma, Kexin Fei, Jiawei Lin, Yu-Mei Xia, Haiping |
author_facet | Liu, Hai-Cheng Ruan, Kaidong Ma, Kexin Fei, Jiawei Lin, Yu-Mei Xia, Haiping |
author_sort | Liu, Hai-Cheng |
collection | PubMed |
description | Azulene-based conjugated systems are of great interests due to their unusual structures and photophysical properties. Incorporation of a transition metal into azulene skeleton presents an intriguing opportunity to combine the d(π)-p(π) and p(π)-p(π) conjugated properties. No such metallaazulene skeleton however has been reported to date. Here, we describe our development of an efficient [5 + 2] annulation reaction to rapid construction of a unique metal-containing [5-5-7] scaffold, termed metalla-dual-azulene (MDA), which includes a metallaazulene and a metal-free organic azulene intertwined by sharing the tropylium motif. The two azulene motifs in MDA exhibit distinct reactivities. The azulene motif readily undergoes nucleophilic addition, leading to N-, O- and S-substituted cycloheptanetrienyl species. Demetalation of the metallaazulene moiety occurs when it reacts with (n)Bu(4)NF, which enables highly selective recognition of fluoride anion and a noticeable color change. The practical [5 + 2] annulation methodology, facile functional-group modification, high and selective fluoride detection make this new π-conjugated polycyclic system very suitable for potential applications in photoelectric and sensing materials. |
format | Online Article Text |
id | pubmed-10495402 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-104954022023-09-13 Synthesis of metalla-dual-azulenes with fluoride ion recognition properties Liu, Hai-Cheng Ruan, Kaidong Ma, Kexin Fei, Jiawei Lin, Yu-Mei Xia, Haiping Nat Commun Article Azulene-based conjugated systems are of great interests due to their unusual structures and photophysical properties. Incorporation of a transition metal into azulene skeleton presents an intriguing opportunity to combine the d(π)-p(π) and p(π)-p(π) conjugated properties. No such metallaazulene skeleton however has been reported to date. Here, we describe our development of an efficient [5 + 2] annulation reaction to rapid construction of a unique metal-containing [5-5-7] scaffold, termed metalla-dual-azulene (MDA), which includes a metallaazulene and a metal-free organic azulene intertwined by sharing the tropylium motif. The two azulene motifs in MDA exhibit distinct reactivities. The azulene motif readily undergoes nucleophilic addition, leading to N-, O- and S-substituted cycloheptanetrienyl species. Demetalation of the metallaazulene moiety occurs when it reacts with (n)Bu(4)NF, which enables highly selective recognition of fluoride anion and a noticeable color change. The practical [5 + 2] annulation methodology, facile functional-group modification, high and selective fluoride detection make this new π-conjugated polycyclic system very suitable for potential applications in photoelectric and sensing materials. Nature Publishing Group UK 2023-09-11 /pmc/articles/PMC10495402/ /pubmed/37696902 http://dx.doi.org/10.1038/s41467-023-41250-5 Text en © The Author(s) 2023 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 Liu, Hai-Cheng Ruan, Kaidong Ma, Kexin Fei, Jiawei Lin, Yu-Mei Xia, Haiping Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title | Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title_full | Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title_fullStr | Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title_full_unstemmed | Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title_short | Synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
title_sort | synthesis of metalla-dual-azulenes with fluoride ion recognition properties |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10495402/ https://www.ncbi.nlm.nih.gov/pubmed/37696902 http://dx.doi.org/10.1038/s41467-023-41250-5 |
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