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Conjugated 12 Nm Long Oligomers As Molecular Wires In Nanoelectronics
Roar R. Søndergaard, S. Strobel, E. Bundgaard, K. Norrman, A. Hansen, E. Albert, G. Csaba, P. Lugli, M. Tornow, F. C. Krebs
Published 2009 · Chemistry
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We demonstrate a generic synthetic approach to oligophenylenevinylene (OPV) derivative molecules with a molecular length of up to 12 nm and a relatively free choice of end group that can attach to different electrodes such as metallic gold or potentially transition metal oxide semiconductors. OPVs containing 3–19 phenyl units were synthesised by step wise HWE-reactions of a bifunctional OPV-monomer which allowed for complete control of the sizes of the OPVs. Workup and analysis (1H- and 13C-NMR, mass spectrometry and size exclusion chromatography) of each step ensured a high purity of the final products. Final end group functionalities of the OPVs were introduced either as the first step (alcohol) or the last step (thioacetate). We further demonstrate a fabrication method for well defined nanogap electrode devices based on silicon-on-insulator technology, featuring a gap distance of down to 9 nm. Assembling the OPV derivatives onto these devices enabled preliminary investigations of their low-temperature transport properties, revealing a pronounced non-linear current–voltage characteristic at 4.2 K. We studied the electronic states of the molecule by Density Functional Theory (DFT) in order to show the effect of the ligands and of the gold contacts. By using the results of the DFT calculations in a non-equilibrium Green's function model, the current–voltage characteristics of OPVs have been analyzed, showing a good qualitative agreement with the experimental data.
This paper references
Density-functional method for nonequilibrium electron transport
M. Brandbyge (2002)
Synthesis and energy-transfer properties of hydrogen-bonded oligofluorenes.
Stephen P. Dudek (2005)
Electrical properties of Si-SiO(2)-Si nanogaps.
J. Berg (2005)
Syntheses of Oligophenylenevinylenes-Polyisoprene Diblock Copolymers and Their Microphase Separation
W. Li (1999)
Novel synthesis of protected thiol end-capped stilbenes and oligo(phenylenevinylene)s (OPVs).
N. Stuhr-Hansen (2003)
Probing molecular wires: synthesis, structural, and electronic study of donor-acceptor assemblies exhibiting long-range electron transfer.
F. Giacalone (2005)
Influence of Residual Catalyst on the Properties of Conjugated Polyphenylenevinylene Materials: Palladium Nanoparticles and Poor Electrical Performance
F. C. Krebs (2004)
Synthesis of an all-in-one molecule (for organic solar cells).
O. Hagemann (2006)
Synthesis of thioacetate-functionalized cobalt(II) porphyrins and their immobilization on gold surface - Characterization by X-ray photoelectron spectroscopy
A. Éll (2006)
Nanoscale aryleneethynylene oligomers incorporating fluorenone units as electron-dopable molecular wires.
C. Wang (2006)
Lifetimes of organic photovoltaics: Design and synthesis of single oligomer molecules in order to study chemical degradation mechanisms
J. Alstrup (2006)
Plastic Solar Cells
C. J. Brabec (2001)
Electrical properties of a phenylene vinylene oligomer
P. Rendu (1999)
Silicon based nanogap device for studying electrical transport phenomena in molecule-nanoparticle hybrids.
S. Strobel (2008)
Single-molecule charge-transport measurements that reveal technique-dependent perturbations.
D. S. Seferos (2006)
Comparative study of electrochemically directed assembly versus conventional self-assembly of thioacetyl-terminated oligo(phenylene ethynylene)s on gold and platinum surfaces.
L. Cheng (2004)
X-ray photoelectron spectroscopy sulfur 2p study of organic thiol and disulfide binding interactions with gold surfaces
D. G. Castner (1996)
Stepwise Synthesis of Substituted Oligo(phenylenevinylene) via an Orthogonal Approach
T. Maddux (1997)
A novel "double-coupling" strategy for iterative oligothiophene synthesis using orthogonal Si/Ge protection.
A. Spivey (2002)
A silicon-on-insulator vertical nanogap device for electrical transport measurements in aqueous electrolyte solution
S. Strobel (2007)
Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene
N. S. Sariciftci (1992)
Molecular electronics. Synthesis and testing of components.
J. Tour (2000)
Characterization of 6PV phenylene vinylene oligomer thin films
T. Nguyen (1998)
Polymer Light-Emitting Electrochemical Cells
Q. Pei (1995)
Electron transport in molecular junctions
N. Tao (2006)
Fabrication of nanoscale gaps in integrated circuits
R. Krahne (2002)
Electronic excitations of a single molecule contacted in a three-terminal configuration.
E. A. Osorio (2007)
Electronic transport in single molecule junctions: control of the molecule-electrode coupling through intramolecular tunneling barriers.
A. Danilov (2008)
Electrical conduction through single molecules and self-assembled monolayers
H. Akkerman (2008)
Electrical Resistance of Long Conjugated Molecular Wires
Seong Ho Choi (2008)
Conductance of redox-active single molecular junctions: an electrochemical approach
Zhihai Li (2007)
The influence of thermal fluctuations on the electronic transport of alkeno-thiolates
A. Pecchia (2004)
Practical Synthesis of Vinyl-Substitutedp-Phenylenevinylene Oligomers and Their Triethoxysilyl Derivatives
E. Sugiono (2001)
Single-electron transistor of a single organic molecule with access to several redox states
S. Kubatkin (2003)
A brief history of the development of organic and polymeric photovoltaics
H. Spanggaard (2004)
Fabrication of Steady Junctions Consisting of α,ω-Bis(thioacetate) Oligo(p-phenylene vinylene)s in Nanogap Electrodes
Tien-Tzu Liang (2006)
First-principles calculation of transport properties of a molecular device
Di Ventra M (2000)
Molecular junctions composed of oligothiophene dithiol-bridged gold nanoparticles exhibiting photoresponsive properties.
W. Huang (2005)
Novel one-dimensional nanogap created with standard optical lithography and evaporation procedures.
S. Dirk (2005)
Organic rectifying junctions from an electron-accepting molecular wire and an electron-donating phthalocyanine.
G. J. Ashwell (2006)
High-aspect-ratio nanogap electrodes for averaging molecular conductance measurements.
Sebastian M. Luber (2007)
Molecular modeling of poly(p-phenylenevinylene): Synthesis and photophysical properties of oligomers
T. Jiu (2007)
Alligator clips to molecular dimensions.
N. Prokopuk (2008)
Ab initio modeling of quantum transport properties of molecular electronic devices
J. Taylor (2001)
H. Meier (2002)
Laminated fabrication of polymeric photovoltaic diodes
M. Granström (1998)
Synthesis, photophysical properties, and photovoltaic devices of oligo(p-phenylene vinylene)-fullerene dyads
E. Peeters (2000)
Electron Transport in Molecular Wire Junctions
A. Nitzan (2003)
Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells.
M. Jørgensen (2005)
2.5% efficient organic plastic solar cells
S. Shaheen (2001)
Effective Removal and Quantitative Analysis of Pd, Cu, Ni, and Pt Catalysts from Small-Molecule Products
K. T. Nielsen (2006)
Structural study of four complexes of the M-N2S2 type derived from diethylphenylazothioformamide and the metals palladium, platinum, copper and nickel.
K. T. Nielsen (2007)
Multifunctional properties of monodisperse end-functionalized oligophenylenevinylenes
M. Wong (2004)
Nanometre spaced electrodes on a cleaved AlGaAs surface
Sebastian M. Luber (2005)
Integrated optoelectronic devices based on conjugated polymers
Density‐functional method for very large systems with LCAO basis sets
D. Sánchez-Portal (1997)
Removal of Palladium Nanoparticles from Polymer Materials
K. T. Nielsen (2005)
Triarylamines connected via phenylenevinylene segments
H. Detert (2003)
Stepwise and directional synthesis of end-functionalized single-oligomer OPVs and their application in organic solar cells.
M. Jørgensen (2004)
EuRh 2 P 2 の磁気への共有原子価効果 | 文献情報 | J-GLOBAL 科学技術総合リンクセンター
Schmitz Robert (2008)
Molecular three-terminal devices: fabrication and measurements.
H. V. D. van der Zant (2006)
This paper is referenced by
Modeling and Design of Single-Molecule Devices
Ahmed Mahmoud (2014)
Advances and Challenges in the Synthesis of Poly(p-phenylene vinylene)-Based Polymers
Alan J. Blayney (2014)
Conductance enhancement of InAs/InP heterostructure nanowires by surface functionalization with oligo(phenylene vinylene)s.
M. I. Schukfeh (2013)
Dielectrophoretic trapping of DNA-coated gold nanoparticles on silicon based vertical nanogap devices.
S. Strobel (2011)
Synthesis of substituted pyrazolines as inhibitors of Staphylococcus aureus
Teage Kailyn Drinnon (2015)
Polymer Solar Cells – Non Toxic Processing and Stable Polymer Photovoltaic Materials
Roar R. Søndergaard (2012)
Toward Circuit Modeling of Molecular Devices
Ahmed Mahmoud (2014)
Effects of amino-nitro side groups on electron device of oligo p-phenylenevinylene molecular between ZGNR electrodes
X. Li (2015)
DNA as a molecular wire: distance and sequence dependence.
Chris H Wohlgamuth (2013)
Atomistic study on dithiolated oligo-phenylenevinylene gated device
Ahmed Mahmoud (2014)
Selective etching of InP in InAs/InP nanowires resulting in 11 nm nanogaps
M. I. Schukfeh (2015)
First-Principles Study of a Novel Molecular Rectifier
Ahmed Mahmoud (2013)
The Challenge of Synthesizing Oligomers for Molecular Wires
Roar R. Søndergaard (2011)
DNA charge transport over 34 nm.
J. Slinker (2011)
Preferential dewetting of gold thin films on single walled carbon nanotubes to produce nanogap electrodes
T. Kim (2016)
Towards nanometer-spaced silicon contacts to proteins.
M. I. Schukfeh (2016)
"Hairy" poly(3-hexylthiophene) particles prepared via surface-initiated Kumada catalyst-transfer polycondensation.
V. Senkovskyy (2009)
Silicon based nanogap device for investigating electronic transport through 12 nm long oligomers
S. Strobel (2009)
Formation of nanogaps in InAs nanowires by selectively etching embedded InP segments.
M. I. Schukfeh (2014)
Synthesis of covalently linked molecular bridges between silicon electrodes in CMOS-based arrays of vertical Si/SiO2/Si nanogaps.
G. J. Ashwell (2011)
Domino C-C bond formation approaches for the synthesis of α , β-unsaturated carbonyl functionalized stilbenoids and unsymmetrical hydroxy distyrylbenzenes
First-principles study of rectification in bis-2-(5-ethynylthienyl)ethyne molecular junctions.
S. Yuan (2011)
A Nanoparticle Approach towards Morphology Controlled Organic Photovoltaics (OPV)
T. Andersen (2012)
Electron Transfer through Surface-Grown, Ferrocene-Capped Oligophenylene Molecular Wires (5-50 Å) on n-Si(111) Photoelectrodes.
F. Li (2015)
Transport characterization of a gated molecular device with negative differential resistance
A. Mahmoud (2012)
Enhanced oscillatory rectification and negative differential resistance in pentamantane diamondoid-cumulene systems.
Sherif Abdulkader Tawfik (2016)
High-Performance Computing for Theoretical Study of Nanoscale and Molecular Interconnects
R. Topaloglu (2014)