Mono- and Ditopic Bisfunctionalization of Graphene
Kathrin C. Knirsch
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
These authors contributed equally to this work.
Search for more papers by this authorRicarda A. Schäfer
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
These authors contributed equally to this work.
Search for more papers by this authorDr. Frank Hauke
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Andreas Hirsch
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
Search for more papers by this authorKathrin C. Knirsch
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
These authors contributed equally to this work.
Search for more papers by this authorRicarda A. Schäfer
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
These authors contributed equally to this work.
Search for more papers by this authorDr. Frank Hauke
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Andreas Hirsch
Department of Chemistry and Pharmacy & Joint Institute of Advanced Materials and Processes (ZMP), Friedrich-Alexander University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany
Search for more papers by this authorGraphical Abstract
Two sides to the story: The use of two consecutive reduction and covalent addition steps leads to the monotopic and ditopic functionalization of individual graphene layers on substrates (one side blocked) as well as graphene in dispersion (both sides accessible).
Abstract
For the first time, the bisfunctionalization of graphene by employing two successive reduction and covalent bond forming steps is reported. Bulk functionalization in dispersion and functionalization of individual sheets deposited on surfaces have both been carried out. Whereas in the former case attacks from both sides of the basal plane are possible and can lead to strain-free architectures, in the latter case, retrofunctionalizations can become important when the corresponding anion of the addend is a sufficiently good leaving group.
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References
- 1Y. Shao, J. Wang, H. Wu, J. Liu, I. A. Aksay, Y. Lin, Electroanalysis 2010, 22, 1027–1036.
- 2H. Kim, A. A. Abdala, C. W. Macosko, Macromolecules 2010, 43, 6515–6530.
- 3M. Prato, K. Kostarelos, A. Bianco, Acc. Chem. Res. 2008, 41, 60–68.
- 4J. Iehl, J.-F. Nierengarten, Chem. Commun. 2010, 46, 4160–4162.
- 5F. Hörmann, W. Donaubauer, F. Hampel, A. Hirsch, Chem. Eur. J. 2012, 18, 3329–3337.
- 6F. Hörmann, M. Brettreich, W. Donaubauer, F. Hampel, A. Hirsch, Chem. Eur. J. 2013, 19, 2814–2825.
- 7F. Hörmann, A. Hirsch, Chem. Eur. J. 2013, 19, 3188–3197.
- 8A. Gmehling, A. Hirsch, Eur. J. Org. Chem. 2013, 5093–5105.
- 9A. Hirsch, M. Brettreich, Fullerenes: Chemistry and Reactions, VCH, Weinheim, 2004.
10.1002/3527603492 Google Scholar
- 10J. López-Andarias, A. Bolag, C. Nancoz, E. Vauthey, C. Atienza, N. Sakai, N. Martin, S. Matile, Chem. Commun. 2015, 51, 7543–7545.
- 11F. G. Brunetti, M. A. Herrero, J. de M. Muñoz, A. Díaz-Ortiz, J. Alfonsi, M. Meneghetti, M. Prato, E. Vázquez, J. Am. Chem. Soc. 2008, 130, 8094–8100.
- 12Z. Zhao, Z. Yang, Y. Hu, J. Li, X. Fan, Appl. Surf. Sci. 2013, 276, 476–481.
- 13F. Hof, S. Bosch, S. Eigler, F. Hauke, A. Hirsch, J. Am. Chem. Soc. 2013, 135, 18385–18395.
- 14F. Hof, R. A. Schäfer, C. Weiss, F. Hauke, A. Hirsch, Chem. Eur. J. 2014, 20, 16644–16651.
- 15L. Rodríguez-Pérez, R. García, M. Á. Herranz, N. Martín, Chem. Eur. J. 2014, 20, 7278–7286.
- 16J. M. Englert, C. Dotzer, G. Yang, M. Schmid, C. Papp, J. M. Gottfried, H.-P. Steinrück, E. Spiecker, F. Hauke, A. Hirsch, Nat. Chem. 2011, 3, 279–286.
- 17J. M. Englert, K. C. Knirsch, C. Dotzer, B. Butz, F. Hauke, E. Spiecker, A. Hirsch, Chem. Commun. 2012, 48, 5025–5027.
- 18R. A. Schäfer, J. M. Englert, P. Wehrfritz, W. Bauer, F. Hauke, T. Seyller, A. Hirsch, Angew. Chem. Int. Ed. 2013, 52, 754–757; Angew. Chem. 2013, 125, 782–786.
- 19Z. Syrgiannis, B. Gebhardt, C. Dotzer, F. Hauke, R. Graupner, A. Hirsch, Angew. Chem. Int. Ed. 2010, 49, 3322–3325; Angew. Chem. 2010, 122, 3394–3397.
- 20
- 20aR. Kessinger, J. Crassous, A. Herrmann, M. Rüttimann, L. Echegoyen, F. Diederich, Angew. Chem. Int. Ed. 1998, 37, 1919–1922;
10.1002/(SICI)1521-3773(19980803)37:13/14<1919::AID-ANIE1919>3.0.CO;2-X CAS Web of Science® Google ScholarAngew. Chem. 1998, 110, 2022–2025;10.1002/(SICI)1521-3757(19980703)110:13/14<2022::AID-ANGE2022>3.0.CO;2-Q Web of Science® Google Scholar
- 20bN. N. P. Moonen, C. Thilgen, L. Echegoyen, F. Diederich, Chem. Commun. 2000, 335–336.
- 21S. Eigler, A. Hirsch, Angew. Chem. Int. Ed. 2014, 53, 7720–7738; Angew. Chem. 2014, 126, 7852–7872.
- 22J. O. Sofo, A. S. Chaudhari, G. D. Barber, Phys. Rev. B 2007, 75, 153401.
- 23J. M. Englert, P. Vecera, K. C. Knirsch, R. A. Schäfer, F. Hauke, A. Hirsch, ACS Nano 2013, 7, 5472–5482.
- 24M. M. Lucchese, F. Stavale, E. H. Martins Ferreira, C. Vilani, M. V. O. Moutinho, R. B. Capaz, C. A. Achete, A. Jorio, Carbon 2010, 48, 1592–1597.
- 25L. G. Cançado, A. Jorio, E. H. M. Ferreira, F. Stavale, C. A. Achete, R. B. Capaz, M. V. O. Moutinho, A. Lombardo, T. Kulmala, A. C. Ferrari, Nano Lett. 2011, 11, 3190–3196.
- 26N. Hosoya, Y. Akaho, M. Inoue, S. Sahoo, M. Tachibana, Appl. Phys. Lett. 2014, 105, 023108.
