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

doi:10.1007/s12274-014-0569-x

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 journal › Article › peer-review

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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 language	English
Pages (from-to)	870-886
Number of pages	17
Journal	Nano Research
Volume	8
Issue number	3
DOIs	https://doi.org/10.1007/s12274-014-0569-x
Publication status	Published - Mar 2015

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

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.]",

keywords = "cycloaddition, nonlinear optics, porphyrin, reduced graphene oxide",

author = "Aijian Wang and Wang Yu and Zhengguo Xiao and Yinglin Song and Lingliang Long and Cifuentes, {Marie P.} and Humphrey, {Mark G.} and Chi Zhang",

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year = "2015",

month = mar,

doi = "10.1007/s12274-014-0569-x",

language = "English",

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T1 - A 1,3-dipolar cycloaddition protocol to porphyrin-functionalized reduced graphene oxide with a push-pull motif

AU - Wang, Aijian

AU - Yu, Wang

AU - Xiao, Zhengguo

AU - Song, Yinglin

AU - Long, Lingliang

AU - Cifuentes, Marie P.

AU - Humphrey, Mark G.

AU - Zhang, Chi

PY - 2015/3

Y1 - 2015/3

N2 - 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.]

AB - 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.]

KW - cycloaddition

KW - nonlinear optics

KW - porphyrin

KW - reduced graphene oxide

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DO - 10.1007/s12274-014-0569-x

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JO - Nano Research

JF - Nano Research

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ER -

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

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