Photografting Graphene Oxide to Inert Membrane Materials to Impart Antibacterial Activity

Surface modification with bactericides is a promising approach to imparting membrane materials with biofouling resistance. However, chemical modification of membranes made from inert materials, such as polyvinylidene fluoride (PVDF) and polysulfone, is challenging because of the absence of reactive functional groups on these materials. In this study, we develop a facile procedure using benzophenone as an anchor to graft biocidal graphene oxide (GO) to chemically inactive membrane materials. GO nanosheets are first functionalized with benzophenone through an amide coupling reaction. Then, benzophenone-functionalized GO nanosheets are irreversibly grafted to the inert membrane surfaces via benzophenone-initiated cross-linking under ultraviolet irradiation. The binding of GO to the membrane surface is confirmed by scanning electron microscopy and Raman spectroscopy. When exposed to a model bacterium (Escherichia coli), GO-functionalized PVDF and polysulfone membranes exhibit strong antibacterial activity, re...

[1]  Debora F. Rodrigues,et al.  Surface Modification of Membrane Filters Using Graphene and Graphene Oxide-Based Nanomaterials for Bacterial Inactivation and Removal , 2014 .

[2]  Suck Won Hong,et al.  Wrinkled Surface-Mediated Antibacterial Activity of Graphene Oxide Nanosheets. , 2017, ACS applied materials & interfaces.

[3]  M. Elimelech,et al.  Impact of surface functionalization on bacterial cytotoxicity of single-walled carbon nanotubes. , 2012, Environmental science & technology.

[4]  M. Elimelech,et al.  The Future of Seawater Desalination: Energy, Technology, and the Environment , 2011, Science.

[5]  B. Freeman,et al.  Surface Modification of Water Purification Membranes. , 2017, Angewandte Chemie.

[6]  M. Mirjalili,et al.  Using graphene/TiO2 nanocomposite as a new route for preparation of electroconductive, self-cleaning, antibacterial and antifungal cotton fabric without toxicity , 2014, Cellulose.

[7]  Yingshuai Liu,et al.  Oriented immobilization of proteins on solid supports for use in biosensors and biochips: a review , 2015, Microchimica Acta.

[8]  Yijia Xiong,et al.  A Targeted Releasable Affinity Probe (TRAP) for In Vivo Photocrosslinking , 2009, Chembiochem : a European journal of chemical biology.

[9]  M. Ulbricht,et al.  Novel photochemical surface functionalization of polysulfone ultrafiltration membranes for covalent immobilization of biomolecules , 1996 .

[10]  Chuyang Y. Tang,et al.  Membrane cleaning in membrane bioreactors: A review , 2014 .

[11]  D. Rodrigues,et al.  Toxicity of a polymer-graphene oxide composite against bacterial planktonic cells, biofilms, and mammalian cells. , 2012, Nanoscale.

[12]  Juin-Yih Lai,et al.  Pressure-assisted self-assembly technique for fabricating composite membranes consisting of highly ordered selective laminate layers of amphiphilic graphene oxide , 2014 .

[13]  N. Hilal,et al.  A comprehensive review on surface modified polymer membranes for biofouling mitigation , 2015 .

[14]  Masoud Rahimi,et al.  Preparation of a novel antifouling mixed matrix PES membrane by embedding graphene oxide nanoplates , 2014 .

[15]  Jay R. Werber,et al.  Enhanced antibacterial activity through the controlled alignment of graphene oxide nanosheets , 2017, Proceedings of the National Academy of Sciences.

[16]  Patrick Tabeling,et al.  Benzophenone absorption and diffusion in poly(dimethylsiloxane) and its role in graft photo-polymerization for surface modification. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[17]  Zhijun Zhou,et al.  Improving the antifouling property of polysulfone ultrafiltration membrane by incorporation of isocyanate-treated graphene oxide. , 2013, Physical chemistry chemical physics : PCCP.

[18]  Menachem Elimelech,et al.  Thin-film composite forward osmosis membranes functionalized with graphene oxide–silver nanocomposites for biofouling control , 2017 .

[19]  Haifang Wang,et al.  Superior antibacterial activity of zinc oxide/graphene oxide composites originating from high zinc concentration localized around bacteria. , 2014, ACS applied materials & interfaces.

[20]  R. Haag,et al.  High-Antifouling Polymer Brush Coatings on Nonpolar Surfaces via Adsorption-Cross-Linking Strategy. , 2017, ACS applied materials & interfaces.

[21]  M. Reinhard,et al.  Occurrence and Fate of Benzophenone-Type UV Filters in a Tropical Urban Watershed. , 2018, Environmental science & technology.

[22]  G. Prestwich,et al.  The Life of Pi Star: Exploring the Exciting and Forbidden Worlds of the Benzophenone Photophore. , 2016, Chemical reviews.

[23]  Freek Kapteijn,et al.  Evolution of nitrogen functionalities in carbonaceous materials during pyrolysis , 1995 .

[24]  Saul G. Cohen,et al.  Photoreduction by amines , 1973 .

[25]  Menachem Elimelech,et al.  Thin-Film Composite Polyamide Membranes Functionalized with Biocidal Graphene Oxide Nanosheets , 2014 .

[26]  M. Elimelech,et al.  Biofouling Mitigation in Forward Osmosis Using Graphene Oxide Functionalized Thin-Film Composite Membranes. , 2016, Environmental science & technology.

[27]  Menachem Elimelech,et al.  In situ surface chemical modification of thin-film composite forward osmosis membranes for enhanced organic fouling resistance. , 2013, Environmental science & technology.

[28]  Jing Kong,et al.  Antibacterial activity of graphite, graphite oxide, graphene oxide, and reduced graphene oxide: membrane and oxidative stress. , 2011, ACS nano.

[29]  G. Preston,et al.  Photo-induced covalent cross-linking for the analysis of biomolecular interactions. , 2013, Chemical Society reviews.

[30]  R. Car,et al.  Raman spectra of graphite oxide and functionalized graphene sheets. , 2008, Nano letters.

[31]  Menachem Elimelech,et al.  Fabrication of a Desalination Membrane with Enhanced Microbial Resistance through Vertical Alignment of Graphene Oxide , 2018, Environmental Science & Technology Letters.

[32]  Jay R. Werber,et al.  The role of nanotechnology in tackling global water challenges , 2018, Nature Sustainability.

[33]  Huajian Gao,et al.  Graphene microsheets enter cells through spontaneous membrane penetration at edge asperities and corner sites , 2013, Proceedings of the National Academy of Sciences.

[34]  T. Matsuura,et al.  Surface modifications for antifouling membranes. , 2010, Chemical reviews.

[35]  Haiping Fang,et al.  Destructive extraction of phospholipids from Escherichia coli membranes by graphene nanosheets. , 2013, Nature nanotechnology.

[36]  Tao Chen,et al.  Nanotechnology in plant disease management: DNA-directed silver nanoparticles on graphene oxide as an antibacterial against Xanthomonas perforans. , 2013, ACS nano.

[37]  Dukhyun Choi,et al.  Transparent and attachable ionic communicators based on self-cleanable triboelectric nanogenerators , 2018, Nature Communications.

[38]  Feifei Zhang,et al.  Novel GO-blended PVDF ultrafiltration membranes , 2012 .

[39]  Menachem Elimelech,et al.  Antimicrobial Properties of Graphene Oxide Nanosheets: Why Size Matters. , 2015, ACS nano.

[40]  Laura H Arias Chavez,et al.  Antimicrobial Electrospun Biopolymer Nanofiber Mats Functionalized with Graphene Oxide-Silver Nanocomposites. , 2015, ACS applied materials & interfaces.

[41]  G. Molander,et al.  Photochemical Nickel-Catalyzed C–H Arylation: Synthetic Scope and Mechanistic Investigations , 2016, Journal of the American Chemical Society.

[42]  Bing Zhang,et al.  Preparation and characterization of HPEI-GO/PES ultrafiltration membrane with antifouling and antibacterial properties , 2013 .

[43]  Jiye Shi,et al.  Graphene Oxide‐Based Antibacterial Cotton Fabrics , 2013, Advanced healthcare materials.