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Work Function Maps and Surface Topography Characterization of Nitroaromatic-Ended Dendron Films on Graphite

Published online by Cambridge University Press:  28 October 2013

Eliana D. Farías
Affiliation:
Departamento de Fisicoquímica (INFIQC-CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, X5000HUA, Argentina
Verónica Brunetti*
Affiliation:
Departamento de Fisicoquímica (INFIQC-CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, X5000HUA, Argentina
Julieta I. Paez
Affiliation:
Departamento de Química Orgánica (IMBIV-CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, X5000HUA, Argentina
Miriam C. Strumia
Affiliation:
Departamento de Química Orgánica (IMBIV-CONICET), Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, X5000HUA, Argentina
Mario C.G. Passeggi Jr.
Affiliation:
Laboratorio de Superficies e Interfaces (IFIS Litoral, CONICET-UNL), Facultad de Ingeniería Química, Universidad Nacional del Litoral, Santa Fe, S3000GLN, Argentina Departamento de Materiales, Facultad de Ingeniería Química, Universidad Nacional del Litoral, Santa Fe, S3000AOM, Argentina
Julio Ferrón
Affiliation:
Laboratorio de Superficies e Interfaces (IFIS Litoral, CONICET-UNL), Facultad de Ingeniería Química, Universidad Nacional del Litoral, Santa Fe, S3000GLN, Argentina Departamento de Materiales, Facultad de Ingeniería Química, Universidad Nacional del Litoral, Santa Fe, S3000AOM, Argentina
*
*Corresponding author. E-mail: [email protected]
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Abstract

Surface topography and work function maps were simultaneously obtained for carbon surfaces modified by a dendritic molecule: 3,5-Bis (3,5-dinitrobenzoylamino) benzoic acid. The dendrons were spontaneously assembled onto highly ordered pyrolytic graphite samples, exhibiting an increase in the surface potential. This fact is consistent with the incorporation of an electron-acceptor functional group that remains electroactive on the surface.

Type
Materials Applications
Copyright
Copyright © Microscopy Society of America 2014 

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References

Bélanger, D. & Pinson, J. (2011). Electrografting: A powerful method for surface modification. Chem Soc Rev 40(7), 39954048.CrossRefGoogle ScholarPubMed
Cullen, R.J., Jayasundara, D.R., Soldi, L., Cheng, J.J., Dufaure, G. & Colavita, P.E. (2012). Spontaneous grafting of nitrophenyl groups on amorphous carbon thin films: A structure-reactivity investigation. Chem Mater 24(6), 10311040.CrossRefGoogle Scholar
De Feyter, S. & De Schryver, F.C. (2003). Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy. Chem Soc Rev 32(3), 139150.CrossRefGoogle ScholarPubMed
Florio, G.M., Stiso, K.A. & Campanelli, J.S. (2012). Surface patterning of benzenecarboxylic acids: Influence of structure, solvent, and concentration on molecular self-assembly. J Phys Chem C 116(34), 1816018174.CrossRefGoogle Scholar
Hansen, W.N. & Hansen, G.J. (2001). Standard reference surfaces for work function measurements in air. Surf Sci 481(1-3), 172184.CrossRefGoogle Scholar
Hasobe, T. (2012). Photo- and electro-functional self-assembled architectures of porphyrins. Phys Chem Chem Phys 14(46), 1597515987.CrossRefGoogle ScholarPubMed
Hattori, S., Kano, S., Azuma, Y. & Majima, Y. (2010). Surface potential of 1,10-decanedithiol molecules inserted into octanethiol self-assembled monolayers on Au(111). J Phys Chem C 114(18), 81208125.CrossRefGoogle Scholar
Heimel, G., Romaner, L., Zojer, E. & Bredas, J.L. (2008). The interface energetics of self-assembled monolayers on metals. Acc Chem Res 41(6), 721729.CrossRefGoogle ScholarPubMed
Hoppe, H., Glatzel, T., Niggemann, M., Hinsch, A., Lux-Steiner, M.C. & Sariciftci, N.S. (2005). Kelvin probe force microscopy study on conjugated polymer/fullerene bulk heterojunction organic solar cells. Nano Lett 5(2), 269274.CrossRefGoogle Scholar
Horcas, I., Fernández, R., Gómez-Rodríguez, J.M., Colchero, J., Gómez-Herrero, J. & Baro, A.M. (2007). WSXM: A software for scanning probe microscopy and a tool for nanotechnology. Rev Sci Instrum 78(1), 013705-1013705-9.CrossRefGoogle Scholar
Hughes, K.J. & Engstrom, J.R. (2010). Interfacial organic layers: Tailored surface chemistry for nucleation and growth. J Vac Sci Technol A 28(5), 10331059.CrossRefGoogle Scholar
Ishida, Y., Jikei, M. & Kakimoto, M.A. (2000). Rapid synthesis of aromatic polyamide dendrimers by an orthogonal and a double-stage convergent approach. Macromolecules 33(9), 32023211.CrossRefGoogle Scholar
Ivančo, J. (2012). Intrinsic work function of molecular films. Thin Solid Films 520(11), 39753986.CrossRefGoogle Scholar
Kim, S.I., Oh, H.W., Huh, J.W., Ju, B. & Lee, C.W. (2011). Surface potential behaviors of UV treated of Ag anode for high-performance T-OLED by nanotribology. Thin Solid Films 519(20), 68726875.CrossRefGoogle Scholar
Kim, T.W., Yang, Y., Li, F. & Kwan, W.L. (2012). Electrical memory devices based on inorganic/organic nanocomposites. NPG Asia Mater 4(6), e18-1e18-12.CrossRefGoogle Scholar
Klosterman, J.K., Yamauchi, Y. & Fujita, M. (2009). Engineering discrete stacks of aromatic molecules. Chem Soc Rev 38(6), 17141725.CrossRefGoogle ScholarPubMed
Love, C.S., Ashworth, I., Brennan, C., Chechik, V. & Smith, D.K. (2006). Dendron-protected Au nanoparticles—effect of dendritic structure on chemical stability. J Colloid Interface Sci 302(1), 178186.CrossRefGoogle ScholarPubMed
Matis, B.R., Burgess, J.S., Bulat, F.A., Friedman, A.L., Houston, B.H. & Baldwin, J.W. (2012). Surface doping and band gap tunability in hydrogenated graphene. ACS Nano 6(1), 1722.CrossRefGoogle ScholarPubMed
Melitz, W., Shen, J., Kummel, A.C. & Lee, S. (2011). Kelvin probe force microscopy and its application. Surf Sci Rep 66(1), 127.CrossRefGoogle Scholar
Paez, J.I., Froimowicz, P., Baruzzi, A.M., Strumia, M.C. & Brunetti, V. (2008). Attachment of an aromatic dendritic macromolecule to gold surfaces. Electrochem Commun 10(4), 541545.CrossRefGoogle Scholar
Paez, J.I., Martinelli, M., Brunetti, V. & Strumia, M.C. (2012). Dendronization: A useful synthetic strategy to prepare multifunctional materials. Polymers 4(1), 355395.CrossRefGoogle Scholar
Paez, J.I., Strumia, M.C., Passeggi, M.C.G. Jr., Ferrón, J., Baruzzi, A.M. & Brunetti, V. (2009). Spontaneous adsorption of 3,5-bis(3,5-dinitrobenzoylamino) benzoic acid onto carbon. Electrochimica Acta 54(17), 41924197.CrossRefGoogle Scholar
Palermo, V. & Samorì, P. (2007). Molecular self-assembly across multiple length scales. Angewandte Chemie—Int Ed 46(24), 44284432.CrossRefGoogle ScholarPubMed
Park, C., Lee, J. & Kim, C. (2011). Functional supramolecular assemblies derived from dendritic building blocks. Chem Commun 47(44), 1204212056.CrossRefGoogle ScholarPubMed
Pei, Z., Lin, L., Zhang, H., Zhang, L. & Xie, Z. (2010). Self-assembly of 2,6-naphthalenedicarboxylic acid and 4,4′-biphenyldicarboxylic acid on highly oriented pyrolytic graphite and Au(1 1 1) surfaces. Electrochimica Acta 55(27), 82878292.CrossRefGoogle Scholar
Peleshanko, S. & Tsukruk, V.V. (2008). The architectures and surface behavior of highly branched molecules. Prog Polym Sci (Oxford) 33(5), 523580.CrossRefGoogle Scholar
Ramesh, A.R. & Thomas, K.G. (2010). Directional hydrogen bonding controlled 2D self-organization of phenyleneethynylenes: From linear assembly to rectangular network. Chem Commun 46(20), 34573459.CrossRefGoogle ScholarPubMed
Reddy, B.N. & Deepa, M. (2012). Unraveling nanoscale conduction and work function in a poly(3,4-ethylenedioxypyrrole)/carbon nanotube composite by Kelvin probe force microscopy and conducting atomic force microscopy. Electrochimica Acta 70, 228240.CrossRefGoogle Scholar
Saito, N., Hayashi, K., Sugimura, H., Takai, O. & Nakagiri, N. (2001). Surface potentials of patterned organosilane self-assembled monolayers acquired by Kelvin probe force microscopy and ab initio molecular calculation. Chem Phys Lett 349(3-4), 172177.CrossRefGoogle Scholar
Spadafora, E.J., Saint-Aubin, K., Celle, C., Demadrille, R., Grévin, B. & Simonato, J.P. (2012). Work function tuning for flexible transparent electrodes based on functionalized metallic single walled carbon nanotubes. Carbon 50(10), 34593464.CrossRefGoogle Scholar
Surin, M., Samorì, P., Jouaiti, A., Kyritsakas, N. & Hosseini, M.W. (2007). Molecular tectonics on surfaces: Bottom-up fabrication of 1D coordination networks that form 1D and 2D arrays on graphite. Angewandte Chemie—Int Ed 46(1-2), 245249.CrossRefGoogle ScholarPubMed
Wei, Z., Wang, D., Kim, S., Kim, S.Y., Hu, Y., Yakes, M.K., Laracuente, A.R., Dai, Z., Marder, S.R., Berger, C., King, W.P., De Heer, W.A., Sheehan, P.E. & Riedo, E. (2010). Nanoscale tunable reduction of graphene oxide for graphene electronics. Science 328(5984), 13731376.CrossRefGoogle ScholarPubMed
Xu, L., Miao, X., Ying, X. & Deng, W. (2012a). Two-dimensional self-assembled molecular structures formed by the competition of Van der Waals forces and dipole-dipole interactions. J Phys Chem C 116(1), 10611069.CrossRefGoogle Scholar
Xu, L., Miao, X., Zha, B. & Deng, W. (2012b). Self-assembly polymorphism: Solvent-responsive two-dimensional morphologies of 2,7-ditridecyloxy-9-fluorenone by scanning tunneling microscopy. J Phys Chem C 116(30), 1601416022.CrossRefGoogle Scholar
Yan, L., Punckt, C., Aksay, I.A., Mertin, W. & Bacher, G. (2011). Local voltage drop in a single functionalized graphene sheet characterized by Kelvin probe force microscopy. Nano Lett 11(9), 35433549.CrossRefGoogle Scholar
Yang, Y., Miao, X., Liu, G., Xu, L., Wu, T. & Deng, W. (2012). Self-assembly of dendronized non-planar conjugated molecules on a HOPG surface. Appl Surf Sci 263, 7378.CrossRefGoogle Scholar
Yilmaz, N., Ida, S. & Matsumoto, Y. (2009). Electrical conductivities of nanosheets studied by conductive atomic force microscopy. Mater Chem Phys 116(1), 6266.CrossRefGoogle Scholar
Yoosaf, K., Ramesh, A.R., George, J., Suresh, C.H. & George Thomas, K. (2009). Functional control on the 2D self-organization of phenyleneethynylenes. J Phys Chem C 113(27), 1183611843.CrossRefGoogle Scholar