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Reduced graphene oxide (RGO) has been covalently functionalized with porphyrin moieties by two methods: A straightforward Prato reaction (i.e. a 1, 3-dipolar cycloaddition) with sarcosine and a formyl-containing porphyrin, and a stepwise method that involves a 1, 3-dipolar cycloaddition to the RGO surface using 4-hydroxybenzaldehyde, followed by nucleophilic substitution with an appropriate porphyrin. The chemical bonding of porphyrins to the RGO surface has been confirmed by ultraviolet/visible absorption, fluorescence, Fourier-transform infrared, and Raman spectroscopies, X-ray powder diffraction and X-ray photoelectron spectroscopy, transmission electron and atomic force microscopy, and thermogravimetric analysis; this chemical attachment assures efficient electron/energy transfer between RGO and the porphyrin, and affords improved optical nonlinearities compared to those of the RGO precursor and the pristine porphyrin.

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Publication history

Received: 07 June 2014
Revised: 24 August 2014
Accepted: 24 August 2014
Published: 01 October 2014
Issue date: March 2015

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© Tsinghua University Press and Springer-Verlag Heidelberg 2014

Acknowledgements

Acknowledgements

Financial support from the National Natural Science Foundation of China (Nos. 51432006, 50925207 and 51172100), the Ministry of Science and Technology of China for the International Science Linkages Program (Nos. 2009DFA50620 and 2011DFG52970), the Ministry of Education of China for the Changjiang Innovation Research Team (No. IRT1064), the Ministry of Education and the State Administration of Foreign Experts Affairs for the 111 Project (No. B13025), and Jiangsu Innovation Research Team are gratefully acknowledged. M. G. H and M. P. C. thank the Australian Research Council (ARC) for support.

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Email: nanores@tup.tsinghua.edu.cn

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