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Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties
The syntheses of three new [3]radialenes – hexakis(3,5-dimethylpyrazolyl)-, hexakis(3-cyanophenyl)-, and hexakis(3,4-dicyanophenyl)[3]radialene (1–3) – are reported. Compound 3 is obtained in five steps with an excellent yield of 76% in the key step. Compared to that, the respective steps of the syn...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302100/ https://www.ncbi.nlm.nih.gov/pubmed/22423273 http://dx.doi.org/10.3762/bjoc.8.7 |
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author | Avellaneda, Antonio Hollis, Courtney A He, Xin Sumby, Christopher J |
author_facet | Avellaneda, Antonio Hollis, Courtney A He, Xin Sumby, Christopher J |
author_sort | Avellaneda, Antonio |
collection | PubMed |
description | The syntheses of three new [3]radialenes – hexakis(3,5-dimethylpyrazolyl)-, hexakis(3-cyanophenyl)-, and hexakis(3,4-dicyanophenyl)[3]radialene (1–3) – are reported. Compound 3 is obtained in five steps with an excellent yield of 76% in the key step. Compared to that, the respective steps of the syntheses of 1 and 2 result in lower yields. All compounds adopt a double bladed propeller conformation in solution. Compound 3 is considerably more electron deficient than previously reported hexaaryl[3]radialenes, with reduction potentials of −0.06 and −0.45 V in CH(2)Cl(2). The compounds mostly display red fluorescence with large Stokes shifts. |
format | Online Article Text |
id | pubmed-3302100 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-33021002012-03-15 Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties Avellaneda, Antonio Hollis, Courtney A He, Xin Sumby, Christopher J Beilstein J Org Chem Full Research Paper The syntheses of three new [3]radialenes – hexakis(3,5-dimethylpyrazolyl)-, hexakis(3-cyanophenyl)-, and hexakis(3,4-dicyanophenyl)[3]radialene (1–3) – are reported. Compound 3 is obtained in five steps with an excellent yield of 76% in the key step. Compared to that, the respective steps of the syntheses of 1 and 2 result in lower yields. All compounds adopt a double bladed propeller conformation in solution. Compound 3 is considerably more electron deficient than previously reported hexaaryl[3]radialenes, with reduction potentials of −0.06 and −0.45 V in CH(2)Cl(2). The compounds mostly display red fluorescence with large Stokes shifts. Beilstein-Institut 2012-01-11 /pmc/articles/PMC3302100/ /pubmed/22423273 http://dx.doi.org/10.3762/bjoc.8.7 Text en Copyright © 2012, Avellaneda et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Avellaneda, Antonio Hollis, Courtney A He, Xin Sumby, Christopher J Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title | Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title_full | Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title_fullStr | Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title_full_unstemmed | Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title_short | Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties |
title_sort | fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: synthesis, structures, and properties |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302100/ https://www.ncbi.nlm.nih.gov/pubmed/22423273 http://dx.doi.org/10.3762/bjoc.8.7 |
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