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Nano Research

Article Title

A 1,3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif

Authors

Aijian Wang, China–Australia Joint Research Center for Functional Molecular Materials, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China China–Australia Joint Research Center for Functional Molecular Materials, Scientific Research Academy, Jiangsu University, Zhenjiang 212013, China
Wang Yu, China–Australia Joint Research Center for Functional Molecular Materials, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China
Zhengguo Xiao, School of Physical Science and Technology, Soochow University, Suzhou 215006, China
Yinglin Song, School of Physical Science and Technology, Soochow University, Suzhou 215006, China
Lingliang Long, China–Australia Joint Research Center for Functional Molecular Materials, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China
Marie P. Cifuentes, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia
Mark G. Humphrey, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia
Chi Zhang, China–Australia Joint Research Center for Functional Molecular Materials, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, China China–Australia Joint Research Center for Functional Molecular Materials, Scientific Research Academy, Jiangsu University, Zhenjiang 212013, China Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia

Keywords

porphyrin, cycloaddition, reduced graphene oxide, nonlinear optics

Abstract

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.

Graphical Abstract

Publisher

Tsinghua University Press

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