Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures

Ashok Keerthi; Radha Boya; Daniele Rizzo; Valentin  Diez Cabanes; Ian Cheng-Yi  Hou; David Beljonne; Jérôme Cornil; Cinzia Casiraghi; Martin Baumgarten; Klaus Müllen; Akimitsu Narita

doi:10.1021/jacs.7b09031

Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures

Ashok Keerthi, Radha Boya, Daniele Rizzo, Valentin Diez Cabanes, Ian Cheng-Yi Hou, David Beljonne, Jérôme Cornil, Cinzia Casiraghi, Martin Baumgarten, Klaus Müllen, Akimitsu Narita

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Abstract

Edge functionalization of bottom-up synthesized graphene nanoribbons (GNRs) with anthraquinone (AQ) and naphtha-lene/perylene monoimide (NMI/PMI) units has been achieved through a Suzuki coupling of polyphenylene precursors bear-ing bromo groups, prior to the intramolecular oxidative cy-clodehydrogenation. High efficiency of the substitution has been validated by MALDI-TOF MS analysis of the functional-ized precursors and FT-IR, Raman and XPS analyses of the resulting GNRs. Moreover, AFM measurements demonstrated the modulation of the self-assembling behavior of the edge-functionalized GNRs, revealing that GNR-PMI formed an intriguing rectangular network. This result suggests the pos-sibility of programming the supramolecular architecture of GNRs by tuning the functional units.

Original language	English
Journal	Journal of the American Chemical Society
Early online date	3 Nov 2017
DOIs	https://doi.org/10.1021/jacs.7b09031
Publication status	Published - 2017

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Revised Manuscript_JACS-Keerthi et al-2017Accepted author manuscript, 772 KB

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title = "Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures",

abstract = "Edge functionalization of bottom-up synthesized graphene nanoribbons (GNRs) with anthraquinone (AQ) and naphtha-lene/perylene monoimide (NMI/PMI) units has been achieved through a Suzuki coupling of polyphenylene precursors bear-ing bromo groups, prior to the intramolecular oxidative cy-clodehydrogenation. High efficiency of the substitution has been validated by MALDI-TOF MS analysis of the functional-ized precursors and FT-IR, Raman and XPS analyses of the resulting GNRs. Moreover, AFM measurements demonstrated the modulation of the self-assembling behavior of the edge-functionalized GNRs, revealing that GNR-PMI formed an intriguing rectangular network. This result suggests the pos-sibility of programming the supramolecular architecture of GNRs by tuning the functional units.",

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year = "2017",

doi = "10.1021/jacs.7b09031",

language = "English",

journal = "Journal of the American Chemical Society",

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T1 - Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures

AU - Keerthi, Ashok

AU - Boya, Radha

AU - Rizzo, Daniele

AU - Diez Cabanes, Valentin

AU - Hou, Ian Cheng-Yi

AU - Beljonne, David

AU - Cornil, Jérôme

AU - Casiraghi, Cinzia

AU - Baumgarten, Martin

AU - Müllen, Klaus

AU - Narita, Akimitsu

PY - 2017

Y1 - 2017

N2 - Edge functionalization of bottom-up synthesized graphene nanoribbons (GNRs) with anthraquinone (AQ) and naphtha-lene/perylene monoimide (NMI/PMI) units has been achieved through a Suzuki coupling of polyphenylene precursors bear-ing bromo groups, prior to the intramolecular oxidative cy-clodehydrogenation. High efficiency of the substitution has been validated by MALDI-TOF MS analysis of the functional-ized precursors and FT-IR, Raman and XPS analyses of the resulting GNRs. Moreover, AFM measurements demonstrated the modulation of the self-assembling behavior of the edge-functionalized GNRs, revealing that GNR-PMI formed an intriguing rectangular network. This result suggests the pos-sibility of programming the supramolecular architecture of GNRs by tuning the functional units.

AB - Edge functionalization of bottom-up synthesized graphene nanoribbons (GNRs) with anthraquinone (AQ) and naphtha-lene/perylene monoimide (NMI/PMI) units has been achieved through a Suzuki coupling of polyphenylene precursors bear-ing bromo groups, prior to the intramolecular oxidative cy-clodehydrogenation. High efficiency of the substitution has been validated by MALDI-TOF MS analysis of the functional-ized precursors and FT-IR, Raman and XPS analyses of the resulting GNRs. Moreover, AFM measurements demonstrated the modulation of the self-assembling behavior of the edge-functionalized GNRs, revealing that GNR-PMI formed an intriguing rectangular network. This result suggests the pos-sibility of programming the supramolecular architecture of GNRs by tuning the functional units.

U2 - 10.1021/jacs.7b09031

DO - 10.1021/jacs.7b09031

M3 - Article

SN - 0002-7863

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

Edge Functionalization of Structurally Defined Graphene Nanoribbons for Modulating the Self-Assembled Structures

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