Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction

Denis Ari; Jean-Francois Bergamini; Teresa Isabel Loureiro Fidalgo do Vale Rodrigues; Wolfgang Knoll; Charles Cougnon; Essraa Ahmed; Paulius Pobedinskas; Ken Haenen; Nicolas Nuns; Rabah Boukherroub; Sabine Szunerits; Yann R. Leroux

doi:10.1021/acs.chemmater.3c00055

Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction

Denis Ari, Jean-Francois Bergamini, Teresa Isabel Loureiro Fidalgo do Vale Rodrigues, Wolfgang Knoll, Charles Cougnon, Essraa Ahmed, Paulius Pobedinskas, Ken Haenen, Nicolas Nuns, Rabah Boukherroub, Sabine Szunerits, Yann R. Leroux

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Abstract

We propose here a new method to functionalize carbon materials via a catalyzed Diels–Alder reaction. In a Diels–Alder reaction, carbon materials can be used as a diene or a dienophile. Here, carbon materials are used as dienes and alkyne-terminated derivatives as dienophiles. Different carbon materials, i.e., glassy carbon, carbon powder (carbon black), pyrolytic graphite carbon materials, and graphene, were functionalized by alkyne ferrocene derivatives or perfluoro-tagged alkyne molecules and characterized by electrochemical means, atomic force microscopy, and X-ray photoelectron spectroscopy experiments. This method allows for the rapid functionalization of carbon materials in mild conditions with high surface coverage.

Original language	English
Pages (from-to)	4935–4944
Number of pages	10
Journal	Chemistry of Materials
Volume	35
Issue number	13
DOIs	https://doi.org/10.1021/acs.chemmater.3c00055
Publication status	Published - 27 Jun 2023

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Biosensor Technologies

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Ari, D., Bergamini, J.-F., Loureiro Fidalgo do Vale Rodrigues, T. I., Knoll, W., Cougnon, C., Ahmed, E., Pobedinskas, P., Haenen, K., Nuns, N., Boukherroub, R., Szunerits, S., & Leroux, Y. R. (2023). Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction. Chemistry of Materials, 35(13), 4935–4944. https://doi.org/10.1021/acs.chemmater.3c00055

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title = "Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction",

abstract = "We propose here a new method to functionalize carbon materials via a catalyzed Diels–Alder reaction. In a Diels–Alder reaction, carbon materials can be used as a diene or a dienophile. Here, carbon materials are used as dienes and alkyne-terminated derivatives as dienophiles. Different carbon materials, i.e., glassy carbon, carbon powder (carbon black), pyrolytic graphite carbon materials, and graphene, were functionalized by alkyne ferrocene derivatives or perfluoro-tagged alkyne molecules and characterized by electrochemical means, atomic force microscopy, and X-ray photoelectron spectroscopy experiments. This method allows for the rapid functionalization of carbon materials in mild conditions with high surface coverage.",

author = "Denis Ari and Jean-Francois Bergamini and {Loureiro Fidalgo do Vale Rodrigues}, {Teresa Isabel} and Wolfgang Knoll and Charles Cougnon and Essraa Ahmed and Paulius Pobedinskas and Ken Haenen and Nicolas Nuns and Rabah Boukherroub and Sabine Szunerits and Leroux, {Yann R.}",

year = "2023",

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doi = "10.1021/acs.chemmater.3c00055",

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Ari, D, Bergamini, J-F, Loureiro Fidalgo do Vale Rodrigues, TI, Knoll, W, Cougnon, C, Ahmed, E, Pobedinskas, P, Haenen, K, Nuns, N, Boukherroub, R, Szunerits, S & Leroux, YR 2023, 'Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction', Chemistry of Materials, vol. 35, no. 13, pp. 4935–4944. https://doi.org/10.1021/acs.chemmater.3c00055

TY - JOUR

T1 - Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction

AU - Ari, Denis

AU - Bergamini, Jean-Francois

AU - Loureiro Fidalgo do Vale Rodrigues, Teresa Isabel

AU - Knoll, Wolfgang

AU - Cougnon, Charles

AU - Ahmed, Essraa

AU - Pobedinskas, Paulius

AU - Haenen, Ken

AU - Nuns, Nicolas

AU - Boukherroub, Rabah

AU - Szunerits, Sabine

AU - Leroux, Yann R.

PY - 2023/6/27

Y1 - 2023/6/27

N2 - We propose here a new method to functionalize carbon materials via a catalyzed Diels–Alder reaction. In a Diels–Alder reaction, carbon materials can be used as a diene or a dienophile. Here, carbon materials are used as dienes and alkyne-terminated derivatives as dienophiles. Different carbon materials, i.e., glassy carbon, carbon powder (carbon black), pyrolytic graphite carbon materials, and graphene, were functionalized by alkyne ferrocene derivatives or perfluoro-tagged alkyne molecules and characterized by electrochemical means, atomic force microscopy, and X-ray photoelectron spectroscopy experiments. This method allows for the rapid functionalization of carbon materials in mild conditions with high surface coverage.

AB - We propose here a new method to functionalize carbon materials via a catalyzed Diels–Alder reaction. In a Diels–Alder reaction, carbon materials can be used as a diene or a dienophile. Here, carbon materials are used as dienes and alkyne-terminated derivatives as dienophiles. Different carbon materials, i.e., glassy carbon, carbon powder (carbon black), pyrolytic graphite carbon materials, and graphene, were functionalized by alkyne ferrocene derivatives or perfluoro-tagged alkyne molecules and characterized by electrochemical means, atomic force microscopy, and X-ray photoelectron spectroscopy experiments. This method allows for the rapid functionalization of carbon materials in mild conditions with high surface coverage.

U2 - 10.1021/acs.chemmater.3c00055

DO - 10.1021/acs.chemmater.3c00055

M3 - Article

SN - 0897-4756

VL - 35

SP - 4935

EP - 4944

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 13

ER -

Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels–Alder Reaction

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