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Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
Highly distorted polycyclic aromatic hydrocarbons (PAHs) are predicted to be attractive goals in nanoscience owing to the new properties they can exhibit. We have shown that a variety of functionalized distorted heptagon-containing nanographenes can be easily prepared from simple building blocks by...
Autores principales: | , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5357993/ https://www.ncbi.nlm.nih.gov/pubmed/28451246 http://dx.doi.org/10.1039/c6sc02895k |
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author | Márquez, Irene R. Fuentes, Noelia Cruz, Carlos M. Puente-Muñoz, Virginia Sotorrios, Lia Marcos, M. Luisa Choquesillo-Lazarte, Duane Biel, Blanca Crovetto, Luis Gómez-Bengoa, Enrique González, M. Teresa Martin, Ruben Cuerva, Juan M. Campaña, Araceli G. |
author_facet | Márquez, Irene R. Fuentes, Noelia Cruz, Carlos M. Puente-Muñoz, Virginia Sotorrios, Lia Marcos, M. Luisa Choquesillo-Lazarte, Duane Biel, Blanca Crovetto, Luis Gómez-Bengoa, Enrique González, M. Teresa Martin, Ruben Cuerva, Juan M. Campaña, Araceli G. |
author_sort | Márquez, Irene R. |
collection | PubMed |
description | Highly distorted polycyclic aromatic hydrocarbons (PAHs) are predicted to be attractive goals in nanoscience owing to the new properties they can exhibit. We have shown that a variety of functionalized distorted heptagon-containing nanographenes can be easily prepared from simple building blocks by a sequence of Co-catalyzed cyclotrimerization and cyclodehydrogenation reactions. The versatility of this strategy allows easy subsequent enlargement of these nanostructures by Ni-catalyzed cross-coupling and final cyclodehydrogenation reactions. Soluble extended distorted nanographenes 1 and 2 containing heptagon and an edge-shared pentagon–heptagon combination have been synthesized. High distortion of the polycyclic backbone of 2 caused by non-hexagonal rings and a helicene moiety was confirmed by X-ray crystallography. Experimental data reveal promising optical and electronic properties for distorted PAHs with long fluorescence lifetimes (up to 14.5 ns) and low band gaps (down to 2.27 eV). This straightforward and versatile synthetic strategy, the observed long fluorescence lifetimes and the small optical and electrochemical band gaps for the presented compounds may promote the future implementation of distorted graphene molecules in electronic devices. |
format | Online Article Text |
id | pubmed-5357993 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-53579932017-04-27 Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes Márquez, Irene R. Fuentes, Noelia Cruz, Carlos M. Puente-Muñoz, Virginia Sotorrios, Lia Marcos, M. Luisa Choquesillo-Lazarte, Duane Biel, Blanca Crovetto, Luis Gómez-Bengoa, Enrique González, M. Teresa Martin, Ruben Cuerva, Juan M. Campaña, Araceli G. Chem Sci Chemistry Highly distorted polycyclic aromatic hydrocarbons (PAHs) are predicted to be attractive goals in nanoscience owing to the new properties they can exhibit. We have shown that a variety of functionalized distorted heptagon-containing nanographenes can be easily prepared from simple building blocks by a sequence of Co-catalyzed cyclotrimerization and cyclodehydrogenation reactions. The versatility of this strategy allows easy subsequent enlargement of these nanostructures by Ni-catalyzed cross-coupling and final cyclodehydrogenation reactions. Soluble extended distorted nanographenes 1 and 2 containing heptagon and an edge-shared pentagon–heptagon combination have been synthesized. High distortion of the polycyclic backbone of 2 caused by non-hexagonal rings and a helicene moiety was confirmed by X-ray crystallography. Experimental data reveal promising optical and electronic properties for distorted PAHs with long fluorescence lifetimes (up to 14.5 ns) and low band gaps (down to 2.27 eV). This straightforward and versatile synthetic strategy, the observed long fluorescence lifetimes and the small optical and electrochemical band gaps for the presented compounds may promote the future implementation of distorted graphene molecules in electronic devices. Royal Society of Chemistry 2017-02-01 2016-08-31 /pmc/articles/PMC5357993/ /pubmed/28451246 http://dx.doi.org/10.1039/c6sc02895k Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Márquez, Irene R. Fuentes, Noelia Cruz, Carlos M. Puente-Muñoz, Virginia Sotorrios, Lia Marcos, M. Luisa Choquesillo-Lazarte, Duane Biel, Blanca Crovetto, Luis Gómez-Bengoa, Enrique González, M. Teresa Martin, Ruben Cuerva, Juan M. Campaña, Araceli G. Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes |
title | Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
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title_full | Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
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title_fullStr | Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
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title_full_unstemmed | Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
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title_short | Versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes
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title_sort | versatile synthesis and enlargement of functionalized distorted heptagon-containing nanographenes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5357993/ https://www.ncbi.nlm.nih.gov/pubmed/28451246 http://dx.doi.org/10.1039/c6sc02895k |
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