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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...

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Autores principales: Avellaneda, Antonio, Hollis, Courtney A, He, Xin, Sumby, Christopher J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
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.
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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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