A 1,3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif
porphyrin, cycloaddition, reduced graphene oxide, nonlinear optics
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.
Tsinghua University Press
Aijian Wang,Wang Yu,Zhengguo Xiao,Yinglin Song,Lingliang Long,Marie P. Cifuentes,Mark G. Humphrey,Chi Zhang, A 1,3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif. NanoRes.2015, 8(3): 870–886