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Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization

Precise synthesis of graphene nanoribbons (GNRs) is of great interest to chemists and materials scientists because of their unique opto-electronic properties and potential applications in carbon-based nanoelectronics and spintronics. In addition to the tunable edge structure and width, introducing c...

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Autores principales: Obermann, Sebastian, Zheng, Wenhao, Melidonie, Jason, Böckmann, Steffen, Osella, Silvio, Arisnabarreta, Nicolás, Guerrero-León, L. Andrés, Hennersdorf, Felix, Beljonne, David, Weigand, Jan J., Bonn, Mischa, De Feyter, Steven, Hansen, Michael Ryan, Wang, Hai I., Ma, Ji, Feng, Xinliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10430550/
https://www.ncbi.nlm.nih.gov/pubmed/37592977
http://dx.doi.org/10.1039/d3sc02824k
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author Obermann, Sebastian
Zheng, Wenhao
Melidonie, Jason
Böckmann, Steffen
Osella, Silvio
Arisnabarreta, Nicolás
Guerrero-León, L. Andrés
Hennersdorf, Felix
Beljonne, David
Weigand, Jan J.
Bonn, Mischa
De Feyter, Steven
Hansen, Michael Ryan
Wang, Hai I.
Ma, Ji
Feng, Xinliang
author_facet Obermann, Sebastian
Zheng, Wenhao
Melidonie, Jason
Böckmann, Steffen
Osella, Silvio
Arisnabarreta, Nicolás
Guerrero-León, L. Andrés
Hennersdorf, Felix
Beljonne, David
Weigand, Jan J.
Bonn, Mischa
De Feyter, Steven
Hansen, Michael Ryan
Wang, Hai I.
Ma, Ji
Feng, Xinliang
author_sort Obermann, Sebastian
collection PubMed
description Precise synthesis of graphene nanoribbons (GNRs) is of great interest to chemists and materials scientists because of their unique opto-electronic properties and potential applications in carbon-based nanoelectronics and spintronics. In addition to the tunable edge structure and width, introducing curvature in GNRs is a powerful structural feature for their chemi-physical property modification. Here, we report an efficient solution synthesis of the first pyrene-based GNR (PyGNR) with curved geometry via one-pot K-region oxidation and Scholl cyclization of its corresponding well-soluble tetrahydropyrene-based polyphenylene precursor. The efficient A(2)B(2)-type Suzuki polymerization and subsequent Scholl reaction furnishes up to ∼35 nm long curved GNRs bearing cove- and armchair-edges. The construction of model compound 1, as a cutout of PyGNR, from a tetrahydropyrene-based oligophenylene precursor proves the concept and efficiency of the one-pot K-region oxidation and Scholl cyclization, which is clearly revealed by single crystal X-ray diffraction analysis. The structure and optical properties of PyGNR are investigated by Raman, FT-IR, solid-state NMR, STM and UV-Vis analysis with the support of DFT calculations. PyGNR exhibits a narrow optical bandgap of ∼1.4 eV derived from a Tauc plot, qualifying as a low-bandgap GNR. Moreover, THz spectroscopy on PyGNR estimates its macroscopic charge mobility μ as ∼3.6 cm(2) V(−1) s(−1), outperforming several other curved GNRs reported via conventional Scholl reaction.
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spelling pubmed-104305502023-08-17 Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization Obermann, Sebastian Zheng, Wenhao Melidonie, Jason Böckmann, Steffen Osella, Silvio Arisnabarreta, Nicolás Guerrero-León, L. Andrés Hennersdorf, Felix Beljonne, David Weigand, Jan J. Bonn, Mischa De Feyter, Steven Hansen, Michael Ryan Wang, Hai I. Ma, Ji Feng, Xinliang Chem Sci Chemistry Precise synthesis of graphene nanoribbons (GNRs) is of great interest to chemists and materials scientists because of their unique opto-electronic properties and potential applications in carbon-based nanoelectronics and spintronics. In addition to the tunable edge structure and width, introducing curvature in GNRs is a powerful structural feature for their chemi-physical property modification. Here, we report an efficient solution synthesis of the first pyrene-based GNR (PyGNR) with curved geometry via one-pot K-region oxidation and Scholl cyclization of its corresponding well-soluble tetrahydropyrene-based polyphenylene precursor. The efficient A(2)B(2)-type Suzuki polymerization and subsequent Scholl reaction furnishes up to ∼35 nm long curved GNRs bearing cove- and armchair-edges. The construction of model compound 1, as a cutout of PyGNR, from a tetrahydropyrene-based oligophenylene precursor proves the concept and efficiency of the one-pot K-region oxidation and Scholl cyclization, which is clearly revealed by single crystal X-ray diffraction analysis. The structure and optical properties of PyGNR are investigated by Raman, FT-IR, solid-state NMR, STM and UV-Vis analysis with the support of DFT calculations. PyGNR exhibits a narrow optical bandgap of ∼1.4 eV derived from a Tauc plot, qualifying as a low-bandgap GNR. Moreover, THz spectroscopy on PyGNR estimates its macroscopic charge mobility μ as ∼3.6 cm(2) V(−1) s(−1), outperforming several other curved GNRs reported via conventional Scholl reaction. The Royal Society of Chemistry 2023-07-27 /pmc/articles/PMC10430550/ /pubmed/37592977 http://dx.doi.org/10.1039/d3sc02824k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Obermann, Sebastian
Zheng, Wenhao
Melidonie, Jason
Böckmann, Steffen
Osella, Silvio
Arisnabarreta, Nicolás
Guerrero-León, L. Andrés
Hennersdorf, Felix
Beljonne, David
Weigand, Jan J.
Bonn, Mischa
De Feyter, Steven
Hansen, Michael Ryan
Wang, Hai I.
Ma, Ji
Feng, Xinliang
Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title_full Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title_fullStr Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title_full_unstemmed Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title_short Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot K-region oxidation and Scholl cyclization
title_sort curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes via one-pot k-region oxidation and scholl cyclization
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10430550/
https://www.ncbi.nlm.nih.gov/pubmed/37592977
http://dx.doi.org/10.1039/d3sc02824k
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