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Nano Research 2015,8 (3) : 870-886 https://doi.org/10.1007/s12274-014-0569-x
Research Article | Issue | Published: 01 October 2014
A 1, 3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif
Show Author's Information Aijian Wang1,2,  Wang Yu1,  Zhengguo Xiao3,  Yinglin Song3,  Lingliang Long1,  Marie P. Cifuentes4,  Mark G. Humphrey4,  Chi Zhang1,2,4( )
China-Australia Joint Research Center for Functional Molecular MaterialsSchool of Chemical and Material Engineering, Jiangnan UniversityWuxi214122China
China-Australia Joint Research Center for Functional Molecular MaterialsScientific Research Academy, Jiangsu UniversityZhenjiang212013China
School of Physical Science and TechnologySoochow UniversitySuzhou215006China
Research School of ChemistryAustralian National UniversityCanberra, ACT0200Australia
Keywords:
porphyrin, cycloaddition, reduced graphene oxide, nonlinear optics
Cite this article:
A. Wang, W. Yu, Z. Xiao, et al. A 1, 3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif. Nano Research. 2015, 8 (3) : 870-886. https://doi.org/10.1007/s12274-014-0569-x.
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Abstract Full text Electronic supplementary material About this article

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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