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Single Molecule Vs. Large Area Design Of Molecular Electronic Devices Incorporating An Efficient 2-aminepyridine Double Anchoring Group.

L. Herrer, A. Ismael, S. Martín, D. C. Milán, J. Serrano, R. Nichols, C. Lambert, P. Cea
Published 2019 · Materials Science, Medicine

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When a molecule is bound to external electrodes by terminal anchor groups, the latter are of paramount importance in determining the electrical conductance of the resulting molecular junction. Here we explore the electrical properties of a molecule with bidentate anchor groups, namely 4,4'-(1,4-phenylenebis(ethyne-2,1-diyl))bis(pyridin-2-amine), in both large area devices and at the single molecule level. We find an electrical conductance of 0.6 × 10-4 G0 and 1.2 × 10-4 G0 for the monolayer and for the single molecule, respectively. These values are approximately one order of magnitude higher than those reported for monodentate materials having the same molecular skeleton. A combination of theory and experiments is employed to understand the conductance of monolayer and single molecule electrical junctions featuring this new multidentate anchor group. Our results demonstrate that the molecule has a tilt angle of 30° with respect to the normal to the surface in the monolayer, while the break-off length in the single molecule junction occurs for molecules having a tilt angle estimated as 40°, which would account for the difference in their conductance values per molecule. The bidentate 2-aminepyridine anchor is of general interest as a contact group, since this terminal functionalized aromatic ring favours binding of the adsorbate to the metal contact resulting in enhanced conductance values.
This paper references
10.1021/ja4015293
Single-molecule conductance of functionalized oligoynes: length dependence and junction evolution.
P. Moreno-García (2013)
10.1126/SCIENCE.1087481
Measurement of Single-Molecule Resistance by Repeated Formation of Molecular Junctions
B. Xu (2003)
10.1021/JP309871D
Effect of Anchoring Groups on Single Molecule Charge Transport through Porphyrins
Zhihai Li (2013)
10.1021/CM062524P
Preparation and characterization of langmuir and langmuir-blodgett films from a nitrile-terminated tolan
G. Pera (2007)
10.1039/c4cs00143e
Single-molecule electronics: from chemical design to functional devices.
L. Sun (2014)
10.1021/JA0607990
Correlation between HOMO alignment and contact resistance in molecular junctions: aromatic thiols versus aromatic isocyanides.
B. Kim (2006)
10.1038/nchem.1891
Ultra stable self-assembled monolayers of N-heterocyclic carbenes on gold.
Cathleen M. Crudden (2014)
10.1021/ja110244j
Fabrication of asymmetric molecular junctions by the oriented assembly of dithiocarbamate rectifiers.
De-qing Gao (2011)
10.1002/chem.201505216
Design and Synthesis of Aviram-Ratner-Type Dyads and Rectification Studies in Langmuir-Blodgett (LB) Films.
Govindasamy Jayamurugan (2016)
10.1039/b802914h
A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety.
Somsakul Watcharinyanon (2008)
10.1088/1367-2630/16/9/093029
GOLLUM:a next-generation simulation tool for electron, thermal and spin transport
J. Ferrer (2014)
10.1021/JP709745Z
A Comprehensive Study of the Single Molecule Conductance of α,ω-Dicarboxylic Acid-Terminated Alkanes
S. Martín (2008)
10.1021/acs.chemrev.6b00746
Chemical Modification of Semiconductor Surfaces for Molecular Electronics.
A. Vilan (2017)
10.1021/JZ100656S
Reliable Formation of Single Molecule Junctions with Air-Stable Diphenylphosphine Linkers
R. Parameswaran (2010)
10.1021/acs.chemrev.6b00595
Large-Area, Ensemble Molecular Electronics: Motivation and Challenges.
A. Vilan (2017)
10.1002/chem.201001181
Metal-molecule-metal junctions in Langmuir-Blodgett films using a new linker: trimethylsilane.
G. Pera (2010)
10.1039/C6TC03268K
Single-molecule junctions for molecular electronics
Yuki Komoto (2016)
10.1038/NATREVMATS.2016.2
Chemical principles of single-molecule electronics
Timothy A Su (2016)
10.1021/JP301854N
Acetylene Used as a New Linker for Molecular Junctions in Phenylene–Ethynylene Oligomer Langmuir–Blodgett Films
Luz M. Ballesteros (2012)
10.1002/anie.201709419
Side-Group-Mediated Mechanical Conductance Switching in Molecular Junctions.
A. Ismael (2017)
10.1021/la104734j
Directionally oriented LB films of an OPE derivative: assembly, characterization, and electrical properties.
L. Ballesteros (2011)
10.1039/c8nr10464f
Electrically transmissive alkyne-anchored monolayers on gold.
Lucía Herrer (2019)
10.1146/annurev-anchem-071114-040118
Single-Molecule Electronics: Chemical and Analytical Perspectives.
R. Nichols (2015)
10.1088/0953-8984/14/11/302
The SIESTA method for ab initio order-N materials simulation
J. M. Soler (2001)
10.1016/J.SUSC.2007.09.059
Investigation on the nature of the chemical link between acetylenic organosilane self-assembled monolayers and Au(111) by means of synchrotron radiation photoelectron spectroscopy and scanning tunneling microscopy
N. Katsonis (2008)
10.1038/nnano.2013.101
Visions for a molecular future.
E. Scheer (2013)
10.1021/ja9084012
Superior contact for single-molecule conductance: electronic coupling of thiolate and isothiocyanate on Pt, Pd, and Au.
Chih-Hung Ko (2010)
10.1039/C5RA03915K
Self-assembly of catecholic ferrocene and electrochemical behavior of its monolayer
Qian Ye (2015)
10.1021/JA0773857
Contact chemistry and single-molecule conductance: a comparison of phosphines, methyl sulfides, and amines.
Y. S. Park (2007)
10.1039/c5nr08708b
Identification of the current path for a conductive molecular wire on a tripodal platform.
M. A. Karimi (2016)
10.1039/C6RA15477H
Low variability of single-molecule conductance assisted by bulky metal–molecule contacts
R. Ferrad'as (2016)
10.1038/ncomms1029
Gate-controlled electron transport in coronenes as a bottom-up approach towards graphene transistors.
I. Díez-Pérez (2010)
10.1021/ja211677q
Conductive molecular silicon.
R. S. Klausen (2012)
10.1002/anie.200902168
Controlled stability of molecular junctions.
D. Dulić (2009)
10.1021/JP510078W
Single Gold Atom Containing Oligo(phenylene)ethynylene: Assembly into LB Films and Electrical Characterization
L. Ballesteros (2015)
10.1021/ja107340t
Single-molecule junctions based on nitrile-terminated biphenyls: a promising new anchoring group.
A. Mishchenko (2011)
10.1016/J.ELECTACTA.2017.11.174
Investigation of the geometrical arrangement and single molecule charge transport in self-assembled monolayers of molecular towers based on tetraphenylmethane tripod
Táňa Sebechlebská (2017)
10.1021/JP072052H
Preparation of ordered films containing a phenylene ethynylene oligomer by the Langmuir-Blodgett technique.
Ana Villares (2007)
10.1039/B201698B
The first direct comparison of self-assembly and Langmuir–Blodgett deposition techniques: Two routes to highly organized monolayers
S. H. Gyepi-Garbrah (2002)
10.1038/S42254-019-0022-X
Concepts in the design and engineering of single-molecule electronic devices
N. Xin (2019)
10.1021/nn9012687
From tunneling to hopping: a comprehensive investigation of charge transport mechanism in molecular junctions based on oligo(p-phenylene ethynylene)s.
Q. Lu (2009)
10.1021/jz500167p
Conductance Switching and Photovoltaic Effect of Ru(II) Complex Molecular Junctions: Role of Complex Properties and the Metal/Molecule Interface.
Jian-chang Li (2014)
10.1039/c3cs35527f
Molecule-electrode interfaces in molecular electronic devices.
Chuancheng Jia (2013)
10.1039/B603149H
Tuning electron transfer through p-phenyleneethynylene molecular wires.
C. Atienza (2006)
10.1039/C7TC03624H
Influence of surface coverage on the formation of 4,4′-bipyridinium (viologen) single molecular junctions
Henrry M. Osorio (2017)
10.1103/PHYSREVB.93.085437
Dynamic bonding of metallic nanocontacts: Insights from experiments and atomistic simulations
M. A. Fernández (2016)
10.1016/J.SYNTHMET.2009.07.036
Unimolecular electronics and rectifiers
Robert Melville Metzger (2009)
10.1088/0953-8984/28/9/094011
Musical molecules: the molecular junction as an active component in audio distortion circuits.
A. Bergren (2016)
10.1021/nl072058i
Amine-gold linked single-molecule circuits: experiment and theory.
S. Y. Quek (2007)
10.1021/acs.jpclett.8b02051
Unconventional Single-Molecule Conductance Behavior for a New Heterocyclic Anchoring Group: Pyrazolyl.
I. L. Herrer (2018)
10.1002/smll.200902227
Revealing the role of anchoring groups in the electrical conduction through single-molecule junctions.
L. Zotti (2010)
10.1002/chem.201203261
Controlling the structural and electrical properties of diacid oligo(phenylene ethynylene) Langmuir-Blodgett films.
L. Ballesteros (2013)
10.3762/bjnano.6.116
Electrical characterization of single molecule and Langmuir–Blodgett monomolecular films of a pyridine-terminated oligo(phenylene-ethynylene) derivative
Henrry M. Osorio (2015)
10.1021/JP4100262
Additive Electron Pathway and Nonadditive Molecular Conductance by Using a Multipodal Bridging Compound
Manabu Kiguchi (2014)
10.1021/CM903270D
Fabrication, Characterization, and Electrical Properties of Langmuir-Blodgett Films of an Acid Terminated Phenylene-Ethynylene Oligomer
Ana Villares (2010)
10.1021/la904180u
Effect of headgroup on electrical conductivity of self-assembled monolayers on mercury: n-alkanethiols versus n-alkaneselenols.
Emel Adaligil (2010)
10.1021/ja209844r
Single molecular conductance of tolanes: experimental and theoretical study on the junction evolution dependent on the anchoring group.
Wenjing Hong (2012)
10.1002/CHEM.200204682
A molecular approach to self-assembly of trimethylsilylacetylene derivatives on gold.
N. Katsonis (2003)
10.1038/nature05037
Dependence of single-molecule junction conductance on molecular conformation
L. Venkataraman (2006)
10.1021/ja909559m
Optimizing single-molecule conductivity of conjugated organic oligomers with carbodithioate linkers.
Yangjun Xing (2010)
10.1021/ja201861k
Influence of binding groups on molecular junction formation.
Carlos R. Arroyo (2011)
10.1002/anie.201107765
Observation of electrochemically controlled quantum interference in a single anthraquinone-based norbornylogous bridge molecule.
N. Darwish (2012)
10.1021/la504056v
Triazatriangulene as binding group for molecular electronics.
Z. Wei (2014)
10.1038/nnano.2009.10
Mechanically controlled binary conductance switching of a single-molecule junction.
S. Y. Quek (2009)
10.1103/PhysRevLett.108.205502
Mechanical annealing of metallic electrodes at the atomic scale.
C. Sabater (2012)
10.1021/acs.chemrev.5b00680
Molecular-Scale Electronics: From Concept to Function.
D. Xiang (2016)
10.1039/c4cs00264d
Incorporating single molecules into electrical circuits. The role of the chemical anchoring group.
E. Leary (2015)
10.1039/c8cc09681c
Probabilistic mapping of single molecule junction configurations as a tool to achieve the desired geometry of asymmetric tripodal molecules.
V. Kolivoška (2019)
10.1021/ja1015348
Conductance and geometry of pyridine-linked single-molecule junctions.
M. Kamenetska (2010)
10.1021/JP044186Q
Relative conductances of alkaneselenolate and alkanethiolate monolayers on Au{111}.
J. Monnell (2005)
10.1021/JA065864K
Effect of anchoring groups on single-molecule conductance: comparative study of thiol-, amine-, and carboxylic-acid-terminated molecules.
F. Chen (2006)
10.1021/JA025568H
A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: a model for poly(phenyleneethynylene).
A. Beeby (2002)
10.1038/nnano.2010.119
Efficient electronic coupling and improved stability with dithiocarbamate-based molecular junctions.
Florian von Wrochem (2010)
10.1021/nl202720y
Electrical transport properties of oligothiophene-based molecular films studied by current sensing atomic force microscopy.
B. L. M. Hendriksen (2011)
10.1002/chem.201703349
Spatial and Lateral Control of Functionality by Rigid Molecular Platforms.
M. Valášek (2017)
10.3762/bjnano.7.34
Rigid multipodal platforms for metal surfaces
M. Valášek (2016)



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