Advanced Materials

Cover image for Vol. 25 Issue 3

Special Issue: Gated Systems for Multifunctional Optoelectronic Devices

January 18, 2013

Volume 25, Issue 3

Pages 293–487

  1. Cover Picture

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    5. Masthead
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    7. Editorial
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    9. Reviews
    10. Communications
    11. Frontispiece
    12. Communications
    13. Research News
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      Photoresponsive Molecules: Photoresponsive Molecules in Well-Defined Nanoscale Environments (Adv. Mater. 3/2013) (page 293)

      Yue Bing Zheng, Bala Krishna Pathem, J. Nathan Hohman, John C. Thomas, Moonhee Kim and Paul S. Weiss

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201370014

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      Paul S. Weiss and co-workers report on page 302 progress toward the precise assembly and measurement of photoresponsive molecules in well-defined environments. The cover depicts the coordinated photoisomerization of a one-dimensional chain of molecules assembled within a domain boundary of a self-assembled monolayer, measured with a scanning tunneling microscope.

  2. Inside Front Cover

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      Photochromic Materials: Photochromic Transduction Layers in Organic Memory Elements (Adv. Mater. 3/2013) (page 294)

      R. Clayton Shallcross, Philipp Zacharias, Anne Köhnen, Peter O. Körner, Eduard Maibach and Klaus Meerholz

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201370015

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      Photochromic molecules provide an intriguing and relatively untapped alternative to traditional materials utilized in organic memory devices. On page 469, Klaus Meerholz and co-workers review the use of photochromic materials, with an emphasis on dithienylethenes, in electrically-addressed organic electronic devices. Recent results for a multifunctional, light-emitting organic memory device incorporating a photochromic transduction layer are discussed in terms of applications in signage and multilevel memory arrays.

  3. Back Cover

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      Nanoparticles: Dual-Responsive Nanoparticles and their Self-Assembly (Adv. Mater. 3/2013) (page 492)

      Sanjib Das, Priyadarshi Ranjan, Pradipta Sankar Maiti, Gurvinder Singh, Gregory Leitus and Rafal Klajn

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201370016

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      Self-assembly of nanoparticles can be controlled independently and/or cooperatively by light and magnetic field, as demonstrated by Rafal Klajn and co-workers on page 422. Dual-responsive nanoparticles are designed by functionalizing magnetic cores with lightresponsive ligands. These materials respond to both light and magnetic fields and can be assembled into various higher-order structures, depending on the relative contributions of these two stimuli. This strategy will enable controlled capture, delivery, and release of molecular/nanosized cargo.

  4. Masthead

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      Masthead: (Adv. Mater. 3/2013)

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201370017

  5. Contents

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    12. Communications
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  6. Editorial

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      Gated Systems for Multifunctional Optoelectronic Devices (page 301)

      Paolo Samorì and Stefan Hecht

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201205030

  7. Progress Reports

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    1. Photoresponsive Molecules in Well-Defined Nanoscale Environments (pages 302–312)

      Yue Bing Zheng, Bala Krishna Pathem, J. Nathan Hohman, John C. Thomas, Moonhee Kim and Paul S. Weiss

      Version of Record online: 30 AUG 2012 | DOI: 10.1002/adma.201201532

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      Functional molecules that respond to external stimuli are assembled on solid substrates as single molecules, pairs or lines of molecules, or two-dimensional clusters via self- and directed assembly in order to test the limits of cooperative action. We discuss our progress in elucidating photoinduced motion and reactions of these molecules and assemblies using scanning tunneling microscopy and surface-enhanced Raman spectroscopy.

    2. Multi-Functional Integration of Organic Field-Effect Transistors (OFETs): Advances and Perspectives (pages 313–330)

      Chong-an Di, Fengjiao Zhang and Daoben Zhu

      Version of Record online: 2 AUG 2012 | DOI: 10.1002/adma.201201502

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      Multi-functional organic field-effect transistors (OFETs), an emerging focus of organic optoelectronic devices, hold great potential for a variety of applications. This report introduces recent progress on multi-functional OFETs including OFETs based sensors, phototransistors, light-emitting transistors, memory cells, and magnetic field-effect OFETs. Key strategies towards multi- functional integration of OFETs, which involves the exploration of functional materials, interfaces modifications, modulation of condensed structures, optimization of device geometry, and device integration, are summarized. Furthermore, remaining challenges and perspectives are discussed, giving a comprehensive overview of multi-functional OFETs.

    3. Organic Switches for Surfaces and Devices (pages 331–348)

      Albert C. Fahrenbach, Scott C. Warren, Jared T. Incorvati, Alyssa-Jennifer Avestro, Jonathan C. Barnes, J. Fraser Stoddart and Bartosz A. Grzybowski

      Version of Record online: 30 AUG 2012 | DOI: 10.1002/adma.201201912

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      The impact of all-organic switches on the properties of surfaces emphasizes the considerable promise these systems possess and paints a bright picture for future applications in molecular electronic and therapeutic applications as well as artificial molecular machine technologies.

  8. Reviews

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    1. Integration of Photoswitchable Proteins, Photosynthetic Reaction Centers and Semiconductor/Biomolecule Hybrids with Electrode Supports for Optobioelectronic Applications (pages 349–377)

      Fuan Wang, Xiaoqing Liu and Itamar Willner

      Version of Record online: 30 AUG 2012 | DOI: 10.1002/adma.201201772

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      The integration of biomolecules with electrode supports provides the grounds for the development of optobioelectronic devices. This is demonstrated with the photonic switching of the bioelectrocatalytic functions of redox proteins by means of photoisomerizable units, the electrical wiring of photosynthetic reaction centers with electrodes and the fabrication of photobioelectrochemical and photobiofuel cells, and the assembly of redox protein/semiconductor quantum dots (QDs) hybrids on electrode surfaces.

    2. Photochromic Materials: More Than Meets The Eye (pages 378–399)

      Junji Zhang, Qi Zou and He Tian

      Version of Record online: 22 AUG 2012 | DOI: 10.1002/adma.201201521

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      Inspired by the smart photoswitchable characteristics of photochromic materials, a variety of light-driven functional materials have been exploited, such as ultrahigh-density optical data storage, molecular switches, logic gates, molecular wires, optic/electronic devices, sensors, bio-imaging and so on. This review commences with a brief description of exciting progress in this field and further development of these photo-switchable systems into practical applications as well as existing challenges are also discussed.

  9. Communications

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    1. Enhancing the Molecular Signature in Molecule-Nanoparticle Networks Via Inelastic Cotunneling (pages 400–404)

      Jean-Francois Dayen, Edwin Devid, Mutta Venkata Kamalakar, Dmitry Golubev, Constant Guédon, Vina Faramarzi, Bernard Doudin and Sense Jan van der Molen

      Version of Record online: 31 AUG 2012 | DOI: 10.1002/adma.201201550

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      Charge transport in networks of nanoparticles linked by molecular spacers is investigated. Remarkably, in the regime where cotunneling dominates, the molecular signature of a device is strongly enhanced. We demonstrate that the resistance ratio of identical networks with different molecular spacers increases dramatically, from an initial value of 50 up to 105, upon entering the cotunneling regime. Our work shows that intrinsic molecular properties can be amplified through nanoscale engineering.

    2. A New Class of Extended Tetrathiafulvalene Cruciform Molecules for Molecular Electronics with Dithiafulvene-4,5-Dithiolate Anchoring Groups (pages 405–409)

      Christian Richard Parker, Zhongming Wei, Carlos R. Arroyo, Karsten Jennum, Tao Li, Marco Santella, Nicolas Bovet, Guangyao Zhao, Wenping Hu, Herre S. J. van der Zant, Marco Vanin, Gemma C. Solomon, Bo W. Laursen, Kasper Nørgaard and Mogens Brøndsted Nielsen

      Version of Record online: 20 AUG 2012 | DOI: 10.1002/adma.201201583

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      Cruciform motifs with two orthogonally oriented π-extended tetrathiafulvalenes and with differently protected thiolate end-groups are synthesized by stepwise coupling reactions. The molecules are subjected to single-molecule conductivity studies in a break-junction and to conducting probe atomic force microscopy studies in a self-assembled monolayer on gold.

    3. Redox-switchable Intramolecular π−π-Stacking of Perylene Bisimide Dyes in a Cyclophane (pages 410–414)

      Felix Schlosser, Michael Moos, Christoph Lambert and Frank Würthner

      Version of Record online: 16 JUL 2012 | DOI: 10.1002/adma.201201266

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      Molecular actuation by stepwise electrochemical reduction is demonstrated for a cyclophane that exhibits a pronounced conformational transition from a closed cavity with cofacially stacked PBIs in the neutral state to an expanded open cavity in the three- and fourfold reduced state.

  10. Frontispiece

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      Photochromes: Quantitative IR Readout of Fulgimide Monolayer Switching on Si(111) Surfaces (Adv. Mater. 3/2013) (page 415)

      Catherine Henry de Villeneuve, Fabian Michalik, Jean Noël Chazalviel, Karola Rück-Braun and P. Allongue

      Version of Record online: 11 JAN 2013 | DOI: 10.1002/adma.201370019

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      Photoactive monolayers on Si(111) surfaces are of considerable interest for nanotechnological applications. Karola Rück-Braun, Catherine Henry de Villeneuve, and co-workers show on page 416 that surface compositions of fulgimide monolayers under visible and UV rradiation can be derived from in situ IR spectroscopy.

  11. Communications

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    1. Quantitative IR Readout of Fulgimide Monolayer Switching on Si(111) Surfaces (pages 416–421)

      Catherine Henry de Villeneuve, Fabian Michalik, Jean Noël Chazalviel, Karola Rück-Braun and P. Allongue

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/adma.201201546

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      Creating photoactive monolayers of photochromes is of considerable technological interest. This paper describes the construct of fulgimide monolayers on silicon surfaces and presents a quantitative IR analysis studies of their composition and switching properties. The scheme on top shows the structure of the starting C-form terminated Si(111) surface and the graph below sketches the surface composition at the photostationnary states under visisble and UV irradiation, as derived from in situ IR spectroscopy after several UV/vis irradiation cycles.

    2. Dual-Responsive Nanoparticles and their Self-Assembly (pages 422–426)

      Sanjib Das, Priyadarshi Ranjan, Pradipta Sankar Maiti, Gurvinder Singh, Gregory Leitus and Rafal Klajn

      Version of Record online: 30 AUG 2012 | DOI: 10.1002/adma.201201734

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      Dual-responsive nanoparticles are designed by functionalizing magnetic cores with light-responsive ligands. These materials respond to both light and magnetic fields and can be assembled into various higher-order structures, depending on the relative contributions of these two stimuli.

    3. A Crown-Ether Loop-Derivatized Oligothiophene Doubly Attached on Gold Surface as Cation-Binding Switchable Molecular Junction (pages 427–431)

      Truong Khoa Tran, Kacem Smaali, Marie Hardouin, Quentin Bricaud, Maïténa Oçafrain, Philippe Blanchard, Stéphane Lenfant, Sylvie Godey, Jean Roncali and Dominique Vuillaume

      Version of Record online: 13 AUG 2012 | DOI: 10.1002/adma.201201668

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      A crown-ether dithiol quaterthiophene is synthesized and immobilized on gold surface by double covalent fixation. UV-vis spectroscopy and cyclic voltammetry show that the corresponding dithioester precursor can complex Pb2+ in solution and that this property is maintained for monolayers of the dithiol on gold. Current-voltage measurements by eutectic GaIn drop contact on the monolayer show a significant increase (up to 1.6 × 103 times) of the current at low bias after Pb2+ complexation.

    4. Large Work Function Shift of Gold Induced by a Novel Perfluorinated Azobenzene-Based Self-Assembled Monolayer (pages 432–436)

      Núria Crivillers, Silvio Osella, Colin Van Dyck, Giovanni M. Lazzerini, David Cornil, Andrea Liscio, Francesco Di Stasio, Shabbir Mian, Oliver Fenwick, Federica Reinders, Markus Neuburger, Emanuele Treossi, Marcel Mayor, Vincenzo Palermo, Franco Cacialli, Jérôme Cornil and Paolo Samorì

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adma.201201737

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      Tune it with light! Self-assembled monolayers on gold based on a chemisorbed novel azobenzene derivative with a perfluorinated terminal phenyl ring are prepared. The modified substrate shows a significant work function increase compared to the bare metal. The photo-conversion between trans and cis isomers chemisorbed on the surface shows great perspectives for being an accessible route to tune the gold properties by means of light.

    5. Luminescent Neutral Platinum Complexes Bearing an Asymmetric N^N^N Ligand for High-Performance Solution-Processed OLEDs (pages 437–442)

      Cristina Cebrián, Matteo Mauro, Dimitrios Kourkoulos, Pierluigi Mercandelli, Dirk Hertel, Klaus Meerholz, Cristian A. Strassert and Luisa De Cola

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/adma.201202123

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      The synthesis and full characterization of new platinum complexes bearing a bulky asymmetric dianionic tridentate ligand is reported. The hindrance of the ligand prevents detrimental intermolecular interactions yielding to highly emitting species in both crystalline state and thin-film. Such properties prompted their successful use in solution-processed OLEDs, showing remarkable external quantum efficiency up to 5.6%.

    6. Inclusion Compound Based Approach to Forming Arrays of Artificial Dipolar Molecular Rotors: A Search for Optimal Rotor Structures (pages 443–448)

      Lukáš Kobr, Ke Zhao, Yongqiang Shen, Richard K. Shoemaker, Charles T. Rogers and Josef Michl

      Version of Record online: 8 OCT 2012 | DOI: 10.1002/adma.201203294

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      Hexagonal tris(o-phenylenedioxy)cyclotriphosphazene (TPP) is used as ahost for organizing dipolar molecular rotor guests into regular trigonal arrays. Inclusion of molecular rotors with transversely dipolar rotators into TPP channels is followed by solid-state nuclear magnetic resonance, diifferential scanning calorimetry, X-ray diffraction, and dielectric spectroscopy. The more polar of the two rotors does not form an inclusion. The second rotor forms two different inclusions differing in crystallite size and the rotational barriers.

  12. Research News

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    1. Reverse Engineering of Monolayers and Nanopatterns (pages 449–455)

      Francesco Zerbetto

      Version of Record online: 1 NOV 2012 | DOI: 10.1002/adma.201201687

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      In a molecularly decorated surface, the molecular tiles are “glued” to the surface by binding constants and possibly further “glued” to each other by cooperativity factors. At odds with mosaics, these “glues” come with the tiles and cannot be removed or supplemented. Binding polynomials quantify glue amounts from experimental data and may predict molecular self-organization on surfaces that can be exploited in organic (opto-)electronics.

    2. Analog Applications of Photochemical Switches (pages 456–461)

      Graeme Copley, Thomas A. Moore, Ana L. Moore and Devens Gust

      Version of Record online: 3 SEP 2012 | DOI: 10.1002/adma.201201744

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      Ensembles of molecules containing photochromes or other molecular switching elements can be used as either binary or analog “devices.” Examples of analog applications are presented. The graphic schematically depicts a molecular signal transducer that is an analogue of a transistor amplifier. A blue light input generates green fluorescence output whose amplitude is regulated by a second, red light input.

    3. Surface-Confined Electroactive Molecules for Multistate Charge Storage Information (pages 462–468)

      M. Mas-Torrent, C. Rovira and J. Veciana

      Version of Record online: 23 JUL 2012 | DOI: 10.1002/adma.201201510

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      Recent advances devoted to the fabrication of charge-storage molecular surface-confined devices exhibiting multiple accessible states are highlighted. These devices would permit the processing of higher memory densities raising great hopes for the devices of the future.

    4. Photochromic Transduction Layers in Organic Memory Elements (pages 469–476)

      R. Clayton Shallcross, Philipp Zacharias, Anne Köhnen, Peter O. Körner, Eduard Maibach and Klaus Meerholz

      Version of Record online: 13 AUG 2012 | DOI: 10.1002/adma.201202186

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      The utilization of photochromic materials, with an emphasis on dithienylethenes (see chemical structure), in electrically-addressed organic electronic devices is reviewed. Recent results for a multifunctional, light-emitting organic memory device incorporating a photochromic transduction layer are discussed for applications in signage (bottom left) and multilevel memory arrays (bottom right).

    5. Advances in Supramolecular Electronics – From Randomly Self-assembled Nanostructures to Addressable Self-Organized Interconnects (pages 477–487)

      Emilie Moulin, Juan-José Cid and Nicolas Giuseppone

      Version of Record online: 12 SEP 2012 | DOI: 10.1002/adma.201201949

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      Recent advances in supramolecular electronics show that self-assembled nanowires made of π-stacked molecules can achieve electrical properties competing with those encountered in the other categories of conducting materials, including carbon nanotubes. In addition, by externally controlling the supramolecular polymerization processes with light and electric field, it becomes possible to accurately position these electroactive wires at nanoscale. The graphical abstract represents triarylamine-based supramolecular interconnects of 80 nm length specifically linking two gold electrodes in a pre-determined position.

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