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

Aijian Wang, Wang Yu, Zhengguo Xiao, Yinglin Song, Lingliang Long, Marie P. Cifuentes, Mark G. Humphrey, Chi Zhang*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    38 Citations (Scopus)

    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.

    [Figure not available: see fulltext.]

    Original languageEnglish
    Pages (from-to)870-886
    Number of pages17
    JournalNano Research
    Volume8
    Issue number3
    DOIs
    Publication statusPublished - Mar 2015

    Fingerprint

    Dive into the research topics of 'A 1,3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif'. Together they form a unique fingerprint.

    Cite this