Electrochemical-coupling layer-by-layer (ECC-LbL) assembly.

Electrochemical-coupling layer-by-layer (ECC-LbL) assembly is introduced as a novel fabrication methodology for preparing layered thin films. This method allows us to covalently immobilize functional units (e.g., porphyrin, fullerene, and fluorene) into thin films having desired thicknesses and designable sequences for both homo- and heteroassemblies while ensuring efficient layer-to-layer electronic interactions. Films were prepared using a conventional electrochemical setup by a simple and inexpensive process from which various layering sequences can be obtained, and the photovoltaic functions of a prototype p/n heterojunction device were demonstrated.

[1]  D. Schuster,et al.  Synthesis and Cation-Mediated Electronic Interactions of Two Novel Classes of Porphyrin−Fullerene Hybrids , 1997 .

[2]  J. McLeskey,et al.  Nanostructured solid-state hybrid photovoltaic cells fabricated by electrostatic layer-by-layer deposition , 2009 .

[3]  Jiaoli Li,et al.  Carbazole-based polymers for organic photovoltaic devices. , 2010, Chemical Society reviews.

[4]  Seiji Taniguchi,et al.  Linkage and Solvent Dependence of Photoinduced Electron Transfer in Zincporphyrin-C60 Dyads , 1996 .

[5]  K. Schanze,et al.  A Water-Soluble Poly(phenylene ethynylene) with Pendant Phosphonate Groups. Synthesis, Photophysics, and Layer-by-Layer Self-Assembled Films† , 2003 .

[6]  M. Rubner,et al.  Molecular-Level Processing of Conjugated Polymers. 4. Layer-by-Layer Manipulation of Polyaniline via Hydrogen-Bonding Interactions , 1997 .

[7]  Michael J. McShane,et al.  Microcapsules as optical biosensors , 2010 .

[8]  C. Legrand,et al.  Optical and electrical characterizations of poly(N-alkylcarbazole) light-emitting diodes. Interpretation of electrical behaviour , 1998 .

[9]  G. Cahiez,et al.  Cobalt-catalyzed cross-coupling reactions. , 2010, Chemical reviews.

[10]  F. Caruso,et al.  Next generation, sequentially assembled ultrathin films: beyond electrostatics. , 2007, Chemical Society reviews.

[11]  Dominique Bagnard,et al.  Polyelectrolyte multilayer-mediated gene delivery for semaphorin signaling pathway control. , 2010, Small.

[12]  S. Jenekhe,et al.  Organometallic Donor−Acceptor Conjugated Polymer Semiconductors: Tunable Optical, Electrochemical, Charge Transport, and Photovoltaic Properties , 2009 .

[13]  P. Schaaf,et al.  Polymer multilayer films obtained by electrochemically catalyzed click chemistry. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[14]  Yoshiharu Sato,et al.  Columnar structure in bulk heterojunction in solution-processable three-layered p-i-n organic photovoltaic devices using tetrabenzoporphyrin precursor and silylmethyl[60]fullerene. , 2009, Journal of the American Chemical Society.

[15]  J. Schlenoff.  Retrospective on the future of polyelectrolyte multilayers. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[16]  Zhiyong Tang,et al.  Biomedical Applications of Layer‐by‐Layer Assembly: From Biomimetics to Tissue Engineering , 2006 .

[17]  Electroluminescence from carbazole dimers , 1997 .

[18]  Hong Xia,et al.  Highly luminescent network films from electrochemical deposition of peripheral carbazole functionalized fluorene oligomer and their applications for light-emitting diodes. , 2006, Chemical communications.

[19]  W. Chan,et al.  Fabrication and optoelectronic properties of novel films based on functionalized multiwalled carbon nanotubes and (phthalocyaninato)ruthenium(II) via coordination bonded layer-by-layer self-assembly. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[20]  K. Schanze,et al.  Photovoltaic cells based on sequentially adsorbed multilayers of conjugated poly(p-phenylene ethynylene)s and a water-soluble fullerene derivative. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[21]  V. Torchilin,et al.  Converting poorly soluble materials into stable aqueous nanocolloids. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[22]  G. Decher,et al.  Covalent layer-by-layer assembly and solvent memory of multilayer films from homobifunctional poly(dimethylsiloxane). , 2010, Angewandte Chemie.

[23]  V. Zucolotto,et al.  Immobilization of biomolecules on nanostructured films for biosensing. , 2010, Biosensors & bioelectronics.

[24]  Norio Miyaura,et al.  Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds , 1995 .

[25]  J. Schlenoff,et al.  Multilayer Assemblies of Redox Polyelectrolytes , 1997 .

[26]  P. Kohli,et al.  Applying polymer chemistry to interfaces: Layer-by-layer and spontaneous growth of covalently bound multilayers , 2000 .

[27]  Gero Decher,et al.  Fuzzy Nanoassemblies: Toward Layered Polymeric Multicomposites , 1997 .

[28]  P. Hammond,et al.  Solid‐State Photovoltaic Thin Films using TiO2, Organic Dyes, and Layer‐by‐Layer Polyelectrolyte Nanocomposites , 2003 .

[29]  S. Fukuzumi,et al.  Porphyrin‐ and Fullerene‐Based Molecular Photovoltaic Devices , 2004 .

[30]  F. D’Souza,et al.  Photoinduced electron transfer in supramolecular systems of fullerenes functionalized with ligands capable of binding to zinc porphyrins and zinc phthalocyanines , 2005 .

[31]  P. Hammond.  Form and Function in Multilayer Assembly: New Applications at the Nanoscale , 2004 .

[32]  C. Luscombe,et al.  Benzo[2,1‐b;3,4‐b′]dithiophene‐based low‐bandgap polymers for photovoltaic applications , 2011 .

[33]  J. Simonet,et al.  The anodic oxidation and polymerization of carbazoles and dicarbazoles N-substituted by polyether chains , 1997 .

[34]  F. Caruso,et al.  Assembly of ultrathin polymer multilayer films by click chemistry. , 2006, Journal of the American Chemical Society.

[35]  Qiang He,et al.  Molecular assembly and application of biomimetic microcapsules. , 2009, Chemical Society reviews.

[36]  Frank Caruso,et al.  Layer-by-layer-assembled capsules and films for therapeutic delivery. , 2010, Small.

[37]  Jian Xu,et al.  Covalent Layer‐by‐Layer Assembly of Conjugated Polymers and CdSe Nanoparticles: Multilayer Structure and Photovoltaic Properties , 2006 .

[38]  Joseph Hemmerlé,et al.  Electrochemically triggered assembly of films: a one-pot morphogen-driven buildup. , 2011, Angewandte Chemie.

[39]  M. Pasini,et al.  Self-Assembled Structures of Semiconductor Nanocrystals and Polymers for Photovoltaics. 2. Multilayers of CdSe Nanocrystals and Oligo(poly)thiophene-Based Molecules. Optical, Electrochemical, Photoelectrochemical, and Photoconductive Properties , 2010 .

[40]  V. Bierbaum,et al.  Gas-phase reactions of organic anions as studied by the flowing afterglow technique , 1981 .

[41]  Jimmy C. Yu,et al.  Semiconductor/biomolecular composites for solar energy applications , 2011 .

[42]  P. Hammond,et al.  Electrochemically enabled polyelectrolyte multilayer devices: from fuel cells to sensors. , 2007, Soft matter.

[43]  Yang Yang,et al.  Multi-source/component spray coating for polymer solar cells. , 2010, ACS nano.

[44]  P. Schaaf,et al.  Spray-on organic/inorganic films: a general method for the formation of functional nano- to microscale coatings. , 2010, Angewandte Chemie.

[45]  Takuzo Aida,et al.  A Cyclic Dimer of Metalloporphyrin Forms a Highly Stable Inclusion Complex with C60 , 1999 .

[46]  Jillian M. Buriak,et al.  Stable Inverted Polymer/Fullerene Solar Cells Using a Cationic Polythiophene Modified PEDOT:PSS Cathodic Interface , 2010 .

[47]  K. Schanze,et al.  Conjugated polyelectrolytes: synthesis, photophysics, and applications. , 2009, Angewandte Chemie.

[48]  E. Negishi,et al.  Palladium-catalyzed alkynylation. , 2003, Chemical reviews.

[49]  Michel Schaer,et al.  The role of carbazole in organic light-emitting devices , 1996 .

[50]  M. Prato,et al.  Electrostatic layer-by-layer construction and characterization of photoelectrochemical solar cells based on water soluble polythiophenes and carbon nanotubes , 2009 .

[51]  Katsuhiko Ariga,et al.  Layer-by-layer assembly as a versatile bottom-up nanofabrication technique for exploratory research and realistic application. , 2007, Physical chemistry chemical physics : PCCP.

[52]  Katsuhiko Ariga,et al.  Biomaterials and biofunctionality in layered macromolecular assemblies. , 2008, Macromolecular bioscience.

[53]  Richard F. Heck,et al.  Palladium-catalyzed reactions of organic halides with olefins , 1979 .

[54]  H. Ohkita,et al.  Fabrication and conductive properties of multilayered ultrathin films designed by layer-by-layer assembly of water-soluble fullerenes. , 2010, Langmuir.

[55]  D. Vautier,et al.  Dynamic Aspects of Films Prepared by a Sequential Deposition of Species: Perspectives for Smart and Responsive Materials , 2011, Advanced materials.

[56]  Jean Paul Remon,et al.  Polymeric multilayer capsules in drug delivery. , 2010, Angewandte Chemie.

[57]  Chen Li,et al.  Polyphenylene-based materials for organic photovoltaics. , 2010, Chemical reviews.

[58]  Bon-Cheol Ku,et al.  Electrostatic Assembly of Conjugated Polymer Thin Layers on Electrospun Nanofibrous Membranes for Biosensors , 2004 .

[59]  Franco Cacialli,et al.  Molecular-scale interface engineering for polymer light-emitting diodes , 2000, Nature.

[60]  Katsuhiko Ariga,et al.  Challenges and breakthroughs in recent research on self-assembly , 2008, Science and technology of advanced materials.

[61]  Y. Lvov,et al.  (-)-Epigallocatechin gallate/gelatin layer-by-layer assembled films and microcapsules. , 2009, Journal of colloid and interface science.

[62]  R. Advíncula,et al.  pH-sensitive bipolar ion-permselective ultrathin films. , 2004, Journal of the American Chemical Society.

[63]  Alain M. Jonas,et al.  Ultrathin polymer coatings by complexation of polyelectrolytes at interfaces: suitable materials, structure and properties , 2000 .

[64]  M. Akashi,et al.  Thermoresponsive Ultrathin Hydrogels Prepared by Sequential Chemical Reactions , 2002 .