Reduction and functionalization of graphene oxide sheets using biomimetic dopamine derivatives in one step.

An easy and environmentally friendly chemical method for the simultaneous reduction and noncovalent functionalization of graphene oxide (GO) using dopamine derivatives is described. The reaction takes place at room temperature under ultrasonication of an aqueous suspension of GO and a dopamine derivative. X-ray photoelectron spectroscopy, FT-IR spectroscopy, and cyclic voltammetry characterizations revealed that the resulting material consists of graphene functionalized with the dopamine derivative. This one-step protocol is applied for simultaneous reduction and functionalization of graphene oxide with a dopamine derivative bearing an azide function. The chemical reactivity of the azide function was demonstrated by a postfunctionalization with ethynylferrocene using the Cu(I) catalyzed 1,3-dipolar cyloaddition.

[1]  Yuanyuan Xie,et al.  Photoactive graphene sheets prepared by "click" chemistry. , 2011, Chemical communications.

[2]  C. Macosko,et al.  Aqueous only route toward graphene from graphite oxide. , 2011, ACS nano.

[3]  S. Tosatti,et al.  Biomimetic surface modifications based on the cyanobacterial iron chelator anachelin. , 2006, Journal of the American Chemical Society.

[4]  Y. Coffinier,et al.  Silicon nanowire arrays-induced graphene oxide reduction under UV irradiation. , 2011, Nanoscale.

[5]  J. Tascón,et al.  Environmentally friendly approaches toward the mass production of processable graphene from graphite oxide , 2011 .

[6]  Chen-Chi M. Ma,et al.  Design and tailoring of a hierarchical graphene-carbon nanotube architecture for supercapacitors , 2011 .

[7]  R. Boukherroub,et al.  Clicking ferrocene groups to boron-doped diamond electrodes. , 2009, Chemical communications.

[8]  T. V. van Beek,et al.  Surface functionalization by strain-promoted alkyne-azide click reactions. , 2011, Angewandte Chemie.

[9]  Yuyan Shao,et al.  Graphene Based Electrochemical Sensors and Biosensors: A Review , 2010 .

[10]  H. Dai,et al.  Chemically Derived, Ultrasmooth Graphene Nanoribbon Semiconductors , 2008, Science.

[11]  Myongsoo Lee,et al.  An amphiphilic pyrene sheet for selective functionalization of graphene. , 2011, Chemical communications.

[12]  Kristopher A Kilian,et al.  Functionalization of acetylene-terminated monolayers on Si(100) surfaces: a click chemistry approach. , 2007, Langmuir : the ACS journal of surfaces and colloids.

[13]  J. Tascón,et al.  Atomic force and scanning tunneling microscopy imaging of graphene nanosheets derived from graphite oxide. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[14]  Sarnjeet S. Dhesi,et al.  Catalyst‐Free Efficient Growth, Orientation and Biosensing Properties of Multilayer Graphene Nanoflake Films with Sharp Edge Planes , 2008 .

[15]  R. Kaner,et al.  Honeycomb carbon: a review of graphene. , 2010, Chemical reviews.

[16]  J. Heath,et al.  A non-oxidative approach toward chemically and electrochemically functionalizing Si(111). , 2006, Journal of the American Chemical Society.

[17]  James M Tour,et al.  Diazonium functionalization of surfactant-wrapped chemically converted graphene sheets. , 2008, Journal of the American Chemical Society.

[18]  Qiushui Chen,et al.  Homogeneous detection of concanavalin A using pyrene-conjugated maltose assembled graphene based on fluorescence resonance energy transfer. , 2011, Biosensors & bioelectronics.

[19]  Pinaki Sengupta,et al.  Synthesis of silver nanoparticles in an aqueous suspension of graphene oxide sheets and its antimicrobial activity. , 2011, Colloids and surfaces. B, Biointerfaces.

[20]  Y. Coffinier,et al.  Preparation of graphene/tetrathiafulvalene nanocomposite switchable surfaces. , 2012, Chemical communications.

[21]  R. Boukherroub,et al.  Label-free detection of lectins on carbohydrate-modified boron-doped diamond surfaces. , 2010, Analytical Chemistry.

[22]  R. Boukherroub,et al.  Functionalization of diamond nanoparticles using "click" chemistry. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[23]  T. Govindaraju,et al.  Covalent modification and exfoliation of graphene oxide using ferrocene. , 2010, Nanoscale.

[24]  J. Xin,et al.  Coating carbon nanotubes by spontaneous oxidative polymerization of dopamine , 2008 .

[25]  G. Wallace,et al.  Processable aqueous dispersions of graphene nanosheets. , 2008, Nature nanotechnology.

[26]  Andre K. Geim,et al.  Electric Field Effect in Atomically Thin Carbon Films , 2004, Science.

[27]  Ying Wang,et al.  Preparation, Structure, and Electrochemical Properties of Reduced Graphene Sheet Films , 2009 .

[28]  Ying Wang,et al.  Application of graphene-modified electrode for selective detection of dopamine , 2009 .

[29]  S. Stankovich,et al.  Synthesis of graphene-based nanosheets via chemical reduction of exfoliated graphite oxide , 2007 .

[30]  M. Jimenez,et al.  A "clickable" titanium surface platform. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[31]  N. Devaraj,et al.  "Clicking" functionality onto electrode surfaces. , 2004, Langmuir : the ACS journal of surfaces and colloids.

[32]  Jiali Zhang,et al.  Reduction of graphene oxide via L-ascorbic acid. , 2010, Chemical communications.

[33]  Wen Jing Yang,et al.  Dopamine-Induced Reduction and Functionalization of Graphene Oxide Nanosheets , 2010 .

[34]  C. Rao,et al.  Selectivity in the Interaction of Electron Donor and Acceptor Molecules with Graphene and Single-Walled Carbon Nanotubes , 2009 .

[35]  Haeshin Lee,et al.  Mussel-Inspired Surface Chemistry for Multifunctional Coatings , 2007, Science.

[36]  K. Novoselov,et al.  Detection of individual gas molecules adsorbed on graphene. , 2006, Nature materials.

[37]  Chen-Zhong Li,et al.  Probing the Electrochemical Properties of Graphene Nanosheets for Biosensing Applications , 2009 .

[38]  A. Govindaraj,et al.  Graphene: the new two-dimensional nanomaterial. , 2009, Angewandte Chemie.

[39]  B. Djafari-Rouhani,et al.  Optical and electrochemical properties of tunable host–guest complexes linked to plasmonic interfaces , 2011 .

[40]  Zhenhua Ni,et al.  Symmetry breaking of graphene monolayers by molecular decoration. , 2009, Physical review letters.

[41]  R. McCreery,et al.  Advanced carbon electrode materials for molecular electrochemistry. , 2008, Chemical reviews.

[42]  Qing Hua Wang,et al.  Click Chemistry on Solution-Dispersed Graphene and Monolayer CVD Graphene , 2011 .

[43]  S. Yao,et al.  One‐Pot Preparation of Polymer–Enzyme–Metallic Nanoparticle Composite Films for High‐Performance Biosensing of Glucose and Galactose , 2009 .