Probing the catalytic activity of porous graphene oxide and the origin of this behaviour

Nature Communications - Tập 3 Số 1
Chenliang Su1, Müge Açık2, Kazuyuki Takai3, Jiong Lu4, Si-jia Hao5, Yi Zheng4, Pingping Wu4, Qiaoliang Bao4, Toshiaki Enoki5, Yves J. Chabal6, Kian Ping Loh4
1Department of Chemistry, Graphene Research Centre, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore).
2University of Texas at Dallas
3Department of Chemistry, Tokyo Institute of Technology, Meguro, Japan
4National University of Singapore;
5Tokyo Inst. of Tech.
6Department of Materials Science and Engineering, University of Texas at Dallas, Richardson, USA

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Clark J. H. Solid acids for green chemistry. Acc. Chem. Res. 35, 791–797 (2002).

Anastas P. T., Kirchhoff M. M. Origins, current status, and future challenges of green chemistry. Acc. Chem. Res. 35, 686–694 (2002).

Leitner W. Green chemistry - Frontiers in benign chemical syntheses and processes. Science 284, 1780–1781 (1999).

Su D. S. et al. Metal-free heterogeneous catalysis for sustainable chemistry. Chemsuschem 3, 169–180 (2010).

Bitter J. H. Nanostructured carbons in catalysis a Janus material-industrial applicability and fundamental insights. J. Mater. Chem 20, 7312–7321 (2010).

Dreyer D. R., Bielawski C. W. Carbocatalysis: heterogeneous carbons finding utility in synthetic chemistry. Chem. Sci. 2, 1233–1240 (2011).

Wang Y., Wang X. C., Antonietti M. Polymeric graphitic carbon nitride as a heterogeneous organocatalyst: from photochemistry to multipurpose catalysis to sustainable chemistry. Angew. Chem. Int. Ed. 51, 68–89 (2012).

Hayashi M. Oxidation using activated carbon and molecular oxygen system. Chem. Rec. 8, 252–267 (2008).

Geim A. K., Novoselov K. S. The rise of graphene. Nat. Mater. 6, 183–191 (2007).

Park S., Ruoff R. S. Chemical methods for the production of graphenes. Nat. Nanotech. 4, 217–224 (2009).

Loh K. P., Bao Q. L., Eda G., Chhowalla M. Graphene oxide as a chemically tunable platform for optical applications. Nat. Chem. 2, 1015–1024 (2010).

Dreyer D. R., Park S., Bielawski C. W., Ruoff R. S. The chemistry of graphene oxide. Chem. Soc. Rev. 39, 228–240 (2010).

Loh K. P., Bao Q. L., Ang P. K., Yang J. X. The chemistry of graphene. J. Mater. Chem. 20, 2277–2289 (2010).

Bai H., Li C., Shi G. Q. Functional composite materials based on chemically converted graphene. Adv. Mater. 23, 1089–1115 (2011).

Machado B. F., Serp P. Graphene-based materials for catalysis. Catal. Sci. Technol. 2, 54–75 (2012).

Dreyer D. R., Jia H. P., Todd A. D., Geng J. X., Bielawski C. W. Graphite oxide: a selective and highly efficient oxidant of thiols and sulfides. Org. Biomol. Chem. 9, 7292–7295 (2011).

Jia H. P., Dreyer D. R., Bielawski C. W. C-H oxidation using graphite oxide. Tetrahedron 67, 4431–4434 (2011).

Dreyer D. R., Jia H. P., Bielawski C. W. Graphene oxide: a convenient carbocatalyst for facilitating oxidation and hydration reactions. Angew. Chem. Int. Ed. 49, 6813–6816 (2010).

Kumar A. V., Rao K. R. Recyclable graphite oxide catalyzed Friedel-Crafts addition of indoles to alpha,beta-unsaturated ketones. Tetrahedron Lett. 52, 5188–5191 (2011).

Verma S. et al. Graphene oxide: an efficient and reusable carbocatalyst for aza-Michael addition of amines to activated alkenes. Chem. Commun. 47, 12673–12675 (2011).

Chauhan S. M. S., Mishra S. Use of graphite oxide and graphene oxide as catalysts in the synthesis of dipyrromethane and calix[4]pyrrole. Molecules 16, 7256–7266 (2011).

Dreyer D. R., Jarvis K. A., Ferreira P. J., Bielawski C. W. Graphite oxide as a carbocatalyst for the preparation of fullerene-reinforced polyester and polyamide nanocomposites. Polym. Chem. 3, 757–766 (2012).

Pyun J. Graphene oxide as catalyst: application of carbon materials beyond nanotechnology. Angew. Chem. Int. Ed. 50, 46–48 (2011).

Gao W., Alemany L. B., Ci L. J., Ajayan P. M. New insights into the structure and reduction of graphite oxide. Nat. Chem. 1, 403–408 (2009).

Bagri A. et al. Structural evolution during the reduction of chemically derived graphene oxide. Nat. Chem. 2, 581–587 (2010).

He W. H. L., Lu L. H. Revisiting the structure of graphene oxide for preparing new-style graphene-based ultraviolet absorbers. Adv. Funct. Mater. 22, 1–8 (2012).

Rourke J. P. et al. The real graphene oxide revealed: Stripping the oxidative debris from the graphene-like sheets. Angew. Chem. Int. Ed. 50, 3173–3177 (2011).

Leadbeater N. E. Cross coupling: when is free really free? Nat. Chem. 2, 1007–1009 (2010).

Prades A., Peris E., Albrecht M. Oxidations and oxidative couplings catalyzed by triazolylidene ruthenium complexes. Organometallics 30, 1162–1167 (2011).

Zhu B. L., Lazar M., Trewyn B. G., Angelici R. J. Aerobic oxidation of amines to imines catalyzed by bulk gold powder and by alumina-supported gold. J. Catal. 260, 1–16 (2008).

Grirrane A., Corma A., Garcia H. Highly active and selective gold catalysts for the aerobic oxidative condensation of benzylamines to imines and one-pot, two-step synthesis of secondary benzylamines. J. Catal. 264, 138–144 (2009).

Chu G. B., Li C. B. Convenient and clean synthesis of imines from primary benzylamines. Org. Biomol. Chem. 8, 4716–4719 (2010).

Li C. J. Cross-dehydrogenative coupling (CDC): Exploring C-C bond formations beyond functional group transformations. Acc. Chem. Res. 42, 335–344 (2009).

Sun C. L., Li B. J., Shi Z. J. Direct C-H transformation via iron catalysis. Chem. Rev. 111, 1293–1314 (2011).

Li Z. P., Bohle D. S., Li C. J. Cu-catalyzed cross-dehydrogenative coupling: A versatile strateav for C-C bond formations via the oxidative activation of sp(3) C-H bonds. Proc. Natl Acad. Sci. USA 103, 8928–8933 (2006).

Li C. J., Trost B. M. Green chemistry for chemical synthesis. Proc. Natl Acad. Sci. USA 105, 13197–13202 (2008).

Segal M. Selling graphene by the ton. Nat. Nanotech. 4, 611–613 (2009).

Liao K. H. et al. Aqueous only route toward graphene from graphite oxide. ACS Nano 5, 1253–1258 (2011).

Acik M. et al. The role of oxygen during thermal reduction of graphene oxide studied by infrared absorption spectroscopy. J. Phys. Chem. C 115, 19761–19781 (2011).

Lerf A., He H. Y., Forster M., Klinowski J. Structure of graphite oxide revisited. J. Phys. Chem. B 102, 4477–4482 (1998).

Takai K., Suzuki T., Enoki T., Nishihara H., Kyotani T. Structure and magnetic properties of curved graphene networks and the effects of bromine and potassium adsorption. Phys. Rev. B 81, 205420 (2010).

Enoki T., Takai K. The edge state of nanographene and the magnetism of the edge-state spins. Solid State Commun. 149, 1144–1150 (2009).

Joly V. L. J. et al. Effect of electron localization on the edge-state spins in a disordered network of nanographene sheets. Phys. Rev. B 81, 115408 (2010).