Bottom-up, Robust Graphene Ribbon Electronics in All-Carbon Molecular Junctions.

electron transport; graphene electronics; graphene ribbons; molecular electronics; molecular junction; 1 ,8-diaminonaphthalene; Electrochemical reductions; Electron delocalization; Electronic coupling; Molecular electronic junction; Materials Science (all); General Materials Science

Abstract :

[en] Large-area molecular electronic junctions consisting of 5-carbon wide graphene ribbons (GR) with lengths of 2-12 nm between carbon electrodes were fabricated by electrochemical reduction of diazotized 1,8-diaminonaphthalene. Their conductance greatly exceeds that observed for other molecular junctions of similar thicknesses, by a factor of >1 × 104 compared to polyphenylenes and >1 × 107 compared to alkane chains. The remarkable increase of conductance of the GR nanolayer results from (i) uninterrupted planarity of fused-arene structure affording extensive π-electron delocalization and (ii) enhanced electronic coupling of molecular layer with the carbon bottom contact by two-point covalent bonding, in agreement with DFT-based simulations.

Disciplines :

Chemistry

Author, co-author :

Supur, Mustafa ; Department of Chemistry, University of Alberta , 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada

Van Dyck, Colin ; Université de Mons - UMONS > Faculté des Sciences > Service Chimie Physique Théorique

Bergren, Adam J; National Institute for Nanotechnology (NINT), National Research Council Canada , 11421 Saskatchewan Drive, Edmonton, Alberta T6G 2M9, Canada

McCreery, Richard L ; Department of Chemistry, University of Alberta , 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada ; National Institute for Nanotechnology (NINT), National Research Council Canada , 11421 Saskatchewan Drive, Edmonton, Alberta T6G 2M9, Canada

Language :

English

Title :

Bottom-up, Robust Graphene Ribbon Electronics in All-Carbon Molecular Junctions.

Publication date :

21 February 2018

Journal title :

ACS Applied Materials and Interfaces

ISSN :

1944-8244

eISSN :

1944-8252

Publisher :

American Chemical Society, United States

Volume :

Issue :

Pages :

6090-6095

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://pubs.acs.org/doi/pdf/10.1021/acsami.7b19305

Research institute :

Matériaux

Funders :

National Research Council Canada
University of Alberta
Natural Sciences and Engineering Research Council of Canada
Alberta Innovates - Technology Futures

Funding text :

This work was supported by the University of Alberta, the National Research Council of Canada, the National Sciences and Engineering Research Council, and Alberta Innovates. We acknowledge the computational resources of the Center for Nanoscale Materials (Argonne National Lab), an Office of Science user facility, supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract DE-AC02-06CH11357.

Available on ORBi UMONS :

since 05 July 2022

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Bibliography

Quinn, J. R.; Foss, F. W.; Venkataraman, L.; Hybertsen, M. S.; Breslow, R. Single-Molecule Junction Conductance through Diaminoacenes J. Am. Chem. Soc. 2007, 129, 6714-6715 10.1021/ja0715804
Kim, W. Y.; Kim, K. S. Tuning Molecular Orbitals in Molecular Electronics and Spintronics Acc. Chem. Res. 2010, 43, 111-120 10.1021/ar900156u
Peplow, M. Rebooting the Molecular Computer ACS Cent. Sci. 2016, 2, 874-877 10.1021/acscentsci.6b00376
Vilan, A.; Aswal, D.; Cahen, D. Large-Area, Ensemble Molecular Electronics: Motivation and Challenges Chem. Rev. 2017, 117, 4248-4286 10.1021/acs.chemrev.6b00595
Jeong, H.; Kim, D.; Xiang, D.; Lee, T. High-Yield Functional Molecular Electronic Devices ACS Nano 2017, 11, 6511-6548 10.1021/acsnano.7b02967
McCreery, R. L.; Bergren, A. J. Progress with Molecular Electronic Junctions: Meeting Experimental Challenges in Design and Fabrication Adv. Mater. 2009, 21, 4303-4322 10.1002/adma.200802850
Sayed, S. Y.; Fereiro, J. A.; Yan, H.; McCreery, R. L.; Bergren, A. J. Charge Transport in Molecular Electronic Junctions: Compression of the Molecular Tunnel Barrier in the Strong Coupling Regime Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 11498-11503 10.1073/pnas.1201557109
Taherinia, D.; Smith, C. E.; Ghosh, S.; Odoh, S. O.; Balhorn, L.; Gagliardi, L.; Cramer, C. J.; Frisbie, C. D. Charge Transport in 4 nm Molecular Wires with Interrupted Conjugation: Combined Experimental and Computational Evidence for Thermally Assisted Polaron Tunneling ACS Nano 2016, 10, 4372-4383 10.1021/acsnano.5b08126
Fraind, A. M.; Sini, G.; Risko, C.; Ryzhkov, L. R.; Brédas, J.-L.; Tovar, J. D. Charge Delocalization through Benzene, Naphthalene, and Anthracene Bridges in π-Conjugated Oligomers: An Experimental and Quantum Chemical Study J. Phys. Chem. B 2013, 117, 6304-6317 10.1021/jp401448a
Sedghi, G.; Sawada, K.; Esdaile, L. J.; Hoffmann, M.; Anderson, H. L.; Bethell, D.; Haiss, W.; Higgins, S. J.; Nichols, R. J. Single Molecule Conductance of Porphyrin Wires with Ultralow Attenuation J. Am. Chem. Soc. 2008, 130, 8582-8583 10.1021/ja802281c
Chen, F.; Tao, N. J. Electron Transport in Single Molecules: From Benzene to Graphene Acc. Chem. Res. 2009, 42, 429-438 10.1021/ar800199a
Jia, C.; Ma, B.; Xin, N.; Guo, X. Carbon Electrode-Molecule Junctions: A Reliable Platform for Molecular Electronics Acc. Chem. Res. 2015, 48, 2565-2575 10.1021/acs.accounts.5b00133
Chen, Y.; Gong, X.-L.; Gai, J.-G. Progress and Challenges in Transfer of Large-Area Graphene Films Adv. Sci. 2016, 3, 1500343 10.1002/advs.201500343
Cai, J.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg, S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X.; Mullen, K.; Fasel, R. Atomically Precise Bottom-Up Fabrication of Graphene Nanoribbons Nature 2010, 466, 470-473 10.1038/nature09211
Sakaguchi, H.; Kawagoe, Y.; Hirano, Y.; Iruka, T.; Yano, M.; Nakae, T. Width-Controlled Sub-Nanometer Graphene Nanoribbon Films Synthesized by Radical-Polymerized Chemical Vapor Deposition Adv. Mater. 2014, 26, 4134-4138 10.1002/adma.201305034
Kimouche, A.; Ervasti, M. M.; Drost, R.; Halonen, S.; Harju, A.; Joensuu, P. M.; Sainio, J.; Liljeroth, P. Ultra-Narrow Metallic Armchair Graphene Nanoribbons Nat. Commun. 2015, 6, 10177 10.1038/ncomms10177
Zhang, H.; Lin, H.; Sun, K.; Chen, L.; Zagranyarski, Y.; Aghdassi, N.; Duhm, S.; Li, Q.; Zhong, D.; Li, Y.; Mullen, K.; Fuchs, H.; Chi, L. On-Surface Synthesis of Rylene-Type Graphene Nanoribbons J. Am. Chem. Soc. 2015, 137, 4022-4025 10.1021/ja511995r
Mahmoud, A. M.; Bergren, A. J.; Pekas, N.; McCreery, R. L. Towards Integrated Molecular Electronic Devices: Characterization of Molecular Layer Integrity During Fabrication Processes Adv. Funct. Mater. 2011, 21, 2273-2281 10.1002/adfm.201002496
Stockhausen, V.; Trippé-Allard, G.; Van Quynh, N.; Ghilane, J.; Lacroix, J.-C. Grafting π-Conjugated Oligomers Incorporating 3,4-Ethylenedioxythiophene (EDOT) and Thiophene Units on Surfaces by Diazonium Electroreduction J. Phys. Chem. C 2015, 119, 19218-19227 10.1021/acs.jpcc.5b05456
Bergren, A. J.; Zeer-Wanklyn, L.; Semple, M.; Pekas, N.; Szeto, B.; McCreery, R. L. Musical Molecules: The Molecular Junction as an Active Component in Audio Distortion Circuits J. Phys.: Condens. Matter 2016, 28, 094011 10.1088/0953-8984/28/9/094011
Bayat, A.; Lacroix, J.-C.; McCreery, R. L. Control of Electronic Symmetry and Rectification through Energy Level Variations in Bilayer Molecular Junctions J. Am. Chem. Soc. 2016, 138, 12287-12296 10.1021/jacs.6b07499
McCreery, R. L. Advanced Carbon Electrode Materials for Molecular Electrochemistry Chem. Rev. 2008, 108, 2646-2687 10.1021/cr068076m
Yang, W.; Lucotti, A.; Tommasini, M.; Chalifoux, W. A. Bottom-Up Synthesis of Soluble and Narrow Graphene Nanoribbons Using Alkyne Benzannulations J. Am. Chem. Soc. 2016, 138, 9137-9144 10.1021/jacs.6b03014
Castiglioni, C.; Mapelli, C.; Negri, F.; Zerbi, G. Origin of the D Line in the Raman Spectrum of Graphite: A Study Based on Raman Frequencies and Intensities of Polycyclic Aromatic Hydrocarbon Molecules J. Chem. Phys. 2001, 114, 963-974 10.1063/1.1329670
Negri, F.; Castiglioni, C.; Tommasini, M.; Zerbi, G. A Computational Study of the Raman Spectra of Large Polycyclic Aromatic Hydrocarbons: Toward Molecularly Defined Subunits of Graphite J. Phys. Chem. A 2002, 106, 3306-3317 10.1021/jp0128473
Supur, M.; Smith, S. R.; McCreery, R. L. Characterization of Growth Patterns of Nanoscale Organic Films on Carbon Electrodes by Surface Enhanced Raman Spectroscopy Anal. Chem. 2017, 89, 6463-6471 10.1021/acs.analchem.7b00362
Rumi, M.; Zerbi, G. Conformational Dependence of Linear and Nonlinear molecular Optical Properties by Ab Initio Methods: The Case of Oligo-p-phenylenes Chem. Phys. 1999, 242, 123-140 10.1016/S0301-0104(99)00010-5
Choi, S. H.; Risko, C.; Delgado, M. C. R.; Kim, B.; Bredas, J.-L.; Frisbie, C. D. Transition from Tunneling to Hopping Transport in Long, Conjugated Oligo-imine Wires Connected to Metals J. Am. Chem. Soc. 2010, 132, 4358-4368 10.1021/ja910547c
Morteza Najarian, A.; McCreery, R. L. Structure Controlled Long-Range Sequential Tunneling in Carbon-Based Molecular Junctions ACS Nano 2017, 11, 3542-3552 10.1021/acsnano.7b00597
Tefashe, U. M.; Nguyen, Q. V.; Lafolet, F.; Lacroix, J.-C.; McCreery, R. L. Robust Bipolar Light Emission and Charge Transport in Symmetric Molecular Junctions J. Am. Chem. Soc. 2017, 139, 7436-7439 10.1021/jacs.7b02563
Amdursky, N.; Marchak, D.; Sepunaru, L.; Pecht, I.; Sheves, M.; Cahen, D. Electronic Transport via Proteins Adv. Mater. 2014, 26, 7142-7161 10.1002/adma.201402304
Luo, L.; Balhorn, L.; Vlaisavljevich, B.; Ma, D.; Gagliardi, L.; Frisbie, C. D. Hopping Transport and Rectifying Behavior in Long Donor-Acceptor Molecular Wires J. Phys. Chem. C 2014, 118, 26485-26497 10.1021/jp507044n
Ho Choi, S.; Kim, B.; Frisbie, C. D. Electrical Resistance of Long Conjugated Molecular Wires Science 2008, 320, 1482-1486 10.1126/science.1156538
Brandbyge, M.; Mozos, J.-L.; Ordejón, P.; Taylor, J.; Stokbro, K. Density-functional method for nonequilibrium electron transport Phys. Rev. B: Condens. Matter Mater. Phys. 2002, 65, 165401 10.1103/PhysRevB.65.165401