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Exfoliation and supramolecular functionalization of graphene with an electron donor perylenediimide derivative

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Abstract

The liquid exfoliation of graphite to few layered graphene sheets together with the non-covalent supramolecular functionalization of exfoliated graphene by the synthesized N,N′-di(2-ethylhexyl)-1-(N′′′′-methylpiperazin-N′′′-yl)perylene-3,4,9,10-tetracarboxydiimide (Pip-PDI) is reported. The aromatic Pip-PDI has the ability to non-covalently interact with the exfoliated graphene sheets, stabilizing them and preventing their reassembly. On the other hand, the presence of the piperazine moiety on the bay position of the PDI core makes it an ideal electron donor, nicely coupled with the electron accepting exfoliated graphene, hence, forming a novel donor–acceptor nanoensemble, which was characterized by complementary spectroscopic and microscopy techniques. Theoretical calculations predicted the absence of a meaningful charge-separated state within the Pip-PDI/graphene ensemble, which was also proven by time-resolved fluorescence and transient absorption measurements.

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Article Open access 09 February 2016

Md. Sajibul Alam Bhuyan, Md. Nizam Uddin, … Sayed Shafayat Hossain

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Acknowledgments

Financial support for this research by the Spanish Ministry of Economy and Competitiveness (Mineco) of Spain (CTQ2014- 55798-R and CTQ2015-71936-REDT), Generalitat Valenciana (Prometeo 2012/010) and by GSRT/NSRF 2007-2013 through action “ARISTEIA II” project FUNGRAPH (3150) “Functionalization of graphene with multichromophoric arrays of photoactive units for energy conversion” is acknowledged. We are indebted to Prof. Nori Shinohara and his group at Nagoya University for kindly acquiring TEM images.

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Authors and Affiliations

  1. Área de Química Orgánica Instituto de Bioingeniería, Universidad Miguel Hernández, Elche, Spain

    Luis Martín-Gomis, Fernando Fernández-Lázaro & Ángela Sastre-Santos

  2. National Hellenic Research Foundation, Theoretical and Physical Chemistry Institute, 48 Vassileos Constantinou Avenue, Athens, 116 35, Greece

    Nikos Karousis, Ioannis D. Petsalakis & Nikos Tagmatarchis

  3. Division of Innovative Research for Drug Design, Institute of Academic Initiatives, Suita, Osaka, 565-0871, Japan

    Kei Ohkubo

  4. Department of Chemistry and Nano Science, Ewha Womans University, Seoul, 120-750, Korea

    Shunichi Fukuzumi

  5. Faculty of Science and Engineering, Meijo University SENTAN, Japan Science and Technology Agency (JST), Nagoya, Aichi, 468-8502, Japan

    Shunichi Fukuzumi

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  1. Luis Martín-Gomis
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Correspondence to Shunichi Fukuzumi, Nikos Tagmatarchis or Ángela Sastre-Santos.

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Martín-Gomis, L., Karousis, N., Fernández-Lázaro, F. et al. Exfoliation and supramolecular functionalization of graphene with an electron donor perylenediimide derivative. Photochem Photobiol Sci 16, 596–605 (2017). https://doi.org/10.1039/c6pp00351f

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