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

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• 作者：Aijian Wang (1) (2)
  Wang Yu (1)
  Zhengguo Xiao (3)
  Yinglin Song (3)
  Lingliang Long (1)
  Marie P. Cifuentes (4)
  Mark G. Humphrey (4)
  Chi Zhang (1) (2) (4)
  
  1. China-Australia Joint Research Center for Functional Molecular Materials ; School of Chemical and Material Engineering ; Jiangnan University ; Wuxi ; 214122 ; China
  2. China-Australia Joint Research Center for Functional Molecular Materials ; Scientific Research Academy ; Jiangsu University ; Zhenjiang ; 212013 ; China
  3. School of Physical Science and Technology ; Soochow University ; Suzhou ; 215006 ; China
  4. Research School of Chemistry ; Australian National University ; Canberra ; ACT 0200 ; Australia
  
• 关键词：porphyrin ; cycloaddition ; reduced graphene oxide ; nonlinear optics
• 刊名：Nano Research
• 出版年：2015
• 出版时间：March 2015
• 年：2015
• 卷：8
• 期：3
• 页码：870-886
• 全文大小：2,739 KB
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• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chinese Library of Science
  Chemistry
  Nanotechnology
  
• 出版者：Tsinghua University Press, co-published with Springer-Verlag GmbH
• ISSN：1998-0000

文摘

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.