ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2003, 125, 51, 16074-16080
RETURN TO ISSUEPREVArticleNEXT

Bonding Self-Assembled, Compact Organophosphonate Monolayers to the Native Oxide Surface of Silicon

View Author Information
Contribution from the Department of Chemistry, Princeton University, Princeton, New Jersey 08544-1009
Cite this: J. Am. Chem. Soc. 2003, 125, 51, 16074–16080
Publication Date (Web):November 25, 2003
https://doi.org/10.1021/ja035956z
Copyright © 2003 American Chemical Society
Request reuse permissions

    Article Views

    5951

    Altmetric

    -

    Citations

    297
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (744 KB)
    Get e-Alerts
    Supporting Info (2)»
    SUBJECTS:

    Abstract

    Abstract Image

    A new method is described to prepare strongly bonded, compact monolayer films of alkyl- or arylphosphonates on the native oxide surface of Si (SiO2/Si). This method is illustrated for octadecyl- and α-quarterthiophene-2-phosphonates. For both cases, AFM shows comprehensive coverage of the SiO2/Si surface. The thickness of the continuous film of 4TP/SiO2/Si was measured both by AFM and by X-ray reflectivity to be ca. 18 Å. Direct gravimetric analysis shows surface coverage by α-quarterthiophene-2-phosphonate to be about 0.66 nmol/cm2, which corresponds to molecular packing in the film close to that of crystalline α-quarterthiophene. Coverage by octadecylphosphonate was ca. 0.90 nmol/cm2, corresponding to a cross-sectional area of about 18.5 Å2/molecule, consistent with close-packed alkyl chains.

    *

    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

    Supporting Information Available

    ARTICLE SECTIONS
    Jump To

    The 1H NMR spectrum (400 MHz; acetone-d6) of α-quarterthiophene-2-phosphonate diethyl ester (aromatic region) (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 297 publications.

    1. Felix Rauh, Florian Pantle, Martin Stutzmann. Morphology, Energy Level Alignment, and Charge Transfer at the Protoporphyrin IX–Semiconductor Interface. Langmuir 2023, 39 (14) , 5095-5106. https://doi.org/10.1021/acs.langmuir.3c00085
    2. Deb Kumar Bhowmick, Adrian Joe Urban, Manfred Bartsch, Björn Braunschweig, Helmut Zacharias. Near-UV-Induced Rapid Formation of Compact Self-Assembled Organophosphonate Monolayers on H-Terminated Si(111) Surfaces. The Journal of Physical Chemistry C 2022, 126 (47) , 19978-19986. https://doi.org/10.1021/acs.jpcc.2c03335
    3. Julien Gay, Agata Lachowicz, Nicolas Blondiaux, Gaëlle A. L. Andreatta. Selective Copper Electroplating on Patterned Self-Assembled Monolayers for Photovoltaic Applications. ACS Applied Nano Materials 2022, 5 (10) , 15954-15961. https://doi.org/10.1021/acsanm.2c04291
    4. Buddini I. Karawdeniya, Adam M. Damry, Krishnan Murugappan, Shridhar Manjunath, Y. M. Nuwan D. Y. Bandara, Colin J. Jackson, Antonio Tricoli, Dragomir Neshev. Surface Functionalization and Texturing of Optical Metasurfaces for Sensing Applications. Chemical Reviews 2022, 122 (19) , 14990-15030. https://doi.org/10.1021/acs.chemrev.1c00990
    5. Julian M. Dlugosch, Henning Seim, Achyut Bora, Takuya Kamiyama, Itai Lieberman, Falk May, Florian Müller-Plathe, Alexei Nefedov, Saurav Prasad, Sebastian Resch, Kai Saller, Christian Seim, Maximilian Speckbacher, Frank Voges, Marc Tornow, Peer Kirsch. Conductance Switching in Liquid Crystal-Inspired Self-Assembled Monolayer Junctions. ACS Applied Materials & Interfaces 2022, 14 (27) , 31044-31053. https://doi.org/10.1021/acsami.2c05264
    6. Lisa Rouvière, Nisreen Al-Hajj, Julien Hunel, Christian Aupetit, Thierry Buffeteau, Luc Vellutini, Emilie Genin. Silane-Based SAMs Deposited by Spin Coating as a Versatile Alternative Process to Solution Immersion. Langmuir 2022, 38 (20) , 6464-6471. https://doi.org/10.1021/acs.langmuir.2c00668
    7. Johannes D. Bartl, Christopher Thomas, Alex Henning, Martina F. Ober, Gökcen Savasci, Bahar Yazdanshenas, Peter S. Deimel, Elena Magnano, Federica Bondino, Patrick Zeller, Luca Gregoratti, Matteo Amati, Claudia Paulus, Francesco Allegretti, Anna Cattani-Scholz, Johannes V. Barth, Christian Ochsenfeld, Bert Nickel, Ian D. Sharp, Martin Stutzmann, Bernhard Rieger. Modular Assembly of Vibrationally and Electronically Coupled Rhenium Bipyridine Carbonyl Complexes on Silicon. Journal of the American Chemical Society 2021, 143 (46) , 19505-19516. https://doi.org/10.1021/jacs.1c09061
    8. Tzu-Ling Liu, Stacey F. Bent. Area-Selective Atomic Layer Deposition on Chemically Similar Materials: Achieving Selectivity on Oxide/Oxide Patterns. Chemistry of Materials 2021, 33 (2) , 513-523. https://doi.org/10.1021/acs.chemmater.0c03227
    9. Dara Bobb-Semple, Li Zeng, Isvar Cordova, David S. Bergsman, Dennis Nordlund, Stacey F. Bent. Substrate-Dependent Study of Chain Orientation and Order in Alkylphosphonic Acid Self-Assembled Monolayers for ALD Blocking. Langmuir 2020, 36 (43) , 12849-12857. https://doi.org/10.1021/acs.langmuir.0c01974
    10. Ian A. VonWald, S. Gaither Frye, Mark M. Moog, Carrie L. Donley, Frank Tsui, Wei You. Initiation and Polymer Density of Conjugated Polymer Brushes. The Journal of Physical Chemistry B 2020, 124 (43) , 9734-9744. https://doi.org/10.1021/acs.jpcb.0c06923
    11. Kai B. Saller, Kung-Ching Liao, Hubert Riedl, Paolo Lugli, Gregor Koblmüller, Jeffrey Schwartz, Marc Tornow. Contact Architecture Controls Conductance in Monolayer Devices. ACS Applied Materials & Interfaces 2020, 12 (25) , 28446-28450. https://doi.org/10.1021/acsami.0c08902
    12. Domenikos Chryssikos, Markus Wiesinger, Oliver Bienek, Hartmut Wiggers, Martin Stutzmann, Anna Cattani-Scholz, Rui N. Pereira. Assembly, Stability, and Electrical Properties of Sparse Crystalline Silicon Nanoparticle Networks Applied to Solution-Processed Field-Effect Transistors. ACS Applied Electronic Materials 2020, 2 (3) , 692-700. https://doi.org/10.1021/acsaelm.9b00786
    13. Barbara P. G. Silva, Bruna Tosco, Daniel Z. de Florio, Vladimir Stepanenko, Frank Würthner, José Fernando Q. Rey, Sergio Brochsztain. Efficient Electronic Coupling in Perylenediimide Multilayered Films on Indium Tin Oxide. The Journal of Physical Chemistry C 2020, 124 (10) , 5541-5551. https://doi.org/10.1021/acs.jpcc.9b11373
    14. Hongliang Chen, Weining Zhang, Mingliang Li, Gen He, Xuefeng Guo. Interface Engineering in Organic Field-Effect Transistors: Principles, Applications, and Perspectives. Chemical Reviews 2020, 120 (5) , 2879-2949. https://doi.org/10.1021/acs.chemrev.9b00532
    15. Eric Hopmann, Abdulhakem Y. Elezzabi. Electrochemical Stability Enhancement of Electrochromic Tungsten Oxide by Self-Assembly of a Phosphonate Protection Layer. ACS Applied Materials & Interfaces 2020, 12 (1) , 1930-1936. https://doi.org/10.1021/acsami.9b19961
    16. Paolo Canepa, Grazia Gonella, Giulia Pinto, Vladimir Grachev, Maurizio Canepa, Ornella Cavalleri. Anchoring of Aminophosphonates on Titanium Oxide for Biomolecular Coupling. The Journal of Physical Chemistry C 2019, 123 (27) , 16843-16850. https://doi.org/10.1021/acs.jpcc.9b04077
    17. Fang Cheng, Hanqi Wang, Wei He, Bingbing Sun, Jing Zhao, Jingping Qu, Qing Wang. New Strategy for Functionalization of Silica Materials via Catalytic Oxa-Michael Reaction of Surface Silanol Groups with Vinyl Sulfones. ACS Sustainable Chemistry & Engineering 2019, 7 (10) , 9112-9120. https://doi.org/10.1021/acssuschemeng.8b05550
    18. Dara Bobb-Semple, Katie Lynn Nardi, Nerissa Draeger, Dennis M. Hausmann, Stacey F. Bent. Area-Selective Atomic Layer Deposition Assisted by Self-Assembled Monolayers: A Comparison of Cu, Co, W, and Ru. Chemistry of Materials 2019, 31 (5) , 1635-1645. https://doi.org/10.1021/acs.chemmater.8b04926
    19. Roberto C. Longo, Kyeongjae Cho, Siegfried Hohmann, Peter Thissen. Mechanism of Phosphorus Transport Through Silicon Oxide During Phosphonic Acid Monolayer Doping. The Journal of Physical Chemistry C 2018, 122 (18) , 10088-10095. https://doi.org/10.1021/acs.jpcc.8b02545
    20. Roland Hönes, Jürgen Rühe. “Nickel Nanoflowers” with Surface-Attached Fluoropolymer Networks by C,H Insertion for the Generation of Metallic Superhydrophobic Surfaces. Langmuir 2018, 34 (18) , 5342-5351. https://doi.org/10.1021/acs.langmuir.7b03915
    21. Maart van Druenen, Gillian Collins, Colm Glynn, Colm O’Dwyer, and Justin D. Holmes . Functionalization of SiO2 Surfaces for Si Monolayer Doping with Minimal Carbon Contamination. ACS Applied Materials & Interfaces 2018, 10 (2) , 2191-2201. https://doi.org/10.1021/acsami.7b16950
    22. Ayelet Vilan, Dinesh Aswal, and David Cahen . Large-Area, Ensemble Molecular Electronics: Motivation and Challenges. Chemical Reviews 2017, 117 (5) , 4248-4286. https://doi.org/10.1021/acs.chemrev.6b00595
    23. William E. Ford, Ffion Abraham, Frank Scholz, Gabriele Nelles, Graham Sandford, and Florian von Wrochem . Spectroscopic Characterization of Fluorinated Benzylphosphonic Acid Monolayers on AlOx/Al Surfaces. The Journal of Physical Chemistry C 2017, 121 (3) , 1690-1703. https://doi.org/10.1021/acs.jpcc.6b11089
    24. Saurabh Das, Byoung Hoon Lee, Roscoe T. H. Linstadt, Keila Cunha, Youli Li, Yair Kaufman, Zachary A. Levine, Bruce H. Lipshutz, Roberto D. Lins, Joan-Emma Shea, Alan J. Heeger, and B. Kollbe Ahn . Molecularly Smooth Self-Assembled Monolayer for High-Mobility Organic Field-Effect Transistors. Nano Letters 2016, 16 (10) , 6709-6715. https://doi.org/10.1021/acs.nanolett.6b03860
    25. Austin W. H. Lee and Byron D. Gates . Rapid Covalent Modification of Silicon Oxide Surfaces through Microwave-Assisted Reactions with Alcohols. Langmuir 2016, 32 (29) , 7284-7293. https://doi.org/10.1021/acs.langmuir.6b00662
    26. Florian Schnetzer, Peter Thissen, Nicolas Giraudo, and Katja Emmerich . Unraveling the Coupled Processes of (De)hydration and Structural Changes in Na+-Saturated Montmorillonite. The Journal of Physical Chemistry C 2016, 120 (28) , 15282-15287. https://doi.org/10.1021/acs.jpcc.6b04986
    27. Sergio A. Paniagua, Anthony J. Giordano, O’Neil L. Smith, Stephen Barlow, Hong Li, Neal R. Armstrong, Jeanne E. Pemberton, Jean-Luc Brédas, David Ginger, and Seth R. Marder . Phosphonic Acids for Interfacial Engineering of Transparent Conductive Oxides. Chemical Reviews 2016, 116 (12) , 7117-7158. https://doi.org/10.1021/acs.chemrev.6b00061
    28. Thibault Alphazan, Laurent Mathey, Martin Schwarzwälder, Tsung-Han Lin, Aaron J. Rossini, Raphaël Wischert, Virginie Enyedi, Hervé Fontaine, Marc Veillerot, Anne Lesage, Lyndon Emsley, Laurent Veyre, François Martin, Chloé Thieuleux, and Christophe Copéret . Monolayer Doping of Silicon through Grafting a Tailored Molecular Phosphorus Precursor onto Oxide-Passivated Silicon Surfaces. Chemistry of Materials 2016, 28 (11) , 3634-3640. https://doi.org/10.1021/acs.chemmater.5b04291
    29. Florian Forato, Hao Liu, Roland Benoit, Franck Fayon, Cathy Charlier, Amina Fateh, Alain Defontaine, Charles Tellier, Daniel R. Talham, Clémence Queffélec, and Bruno Bujoli . Comparison of Zirconium Phosphonate-Modified Surfaces for Immobilizing Phosphopeptides and Phosphate-Tagged Proteins. Langmuir 2016, 32 (22) , 5480-5490. https://doi.org/10.1021/acs.langmuir.6b01020
    30. Jennifer W. Chan, Amy Huang, and Kathryn E. Uhrich . Self-Assembled Amphiphilic Macromolecule Coatings: Comparison of Grafting-From and Grafting-To Approaches for Bioactive Delivery. Langmuir 2016, 32 (20) , 5038-5047. https://doi.org/10.1021/acs.langmuir.6b00524
    31. Alba Córdoba, Margarita Hierro-Oliva, Miguel Ángel Pacha-Olivenza, María Coronada Fernández-Calderón, Joan Perelló, Bernat Isern, María Luisa González-Martín, Marta Monjo, and Joana M. Ramis . Direct Covalent Grafting of Phytate to Titanium Surfaces through Ti–O–P Bonding Shows Bone Stimulating Surface Properties and Decreased Bacterial Adhesion. ACS Applied Materials & Interfaces 2016, 8 (18) , 11326-11335. https://doi.org/10.1021/acsami.6b02533
    32. Bruno Fabre . Functionalization of Oxide-Free Silicon Surfaces with Redox-Active Assemblies. Chemical Reviews 2016, 116 (8) , 4808-4849. https://doi.org/10.1021/acs.chemrev.5b00595
    33. Stephen K. Davidowski and Gregory P. Holland . Solid-State NMR Characterization of Mixed Phosphonic Acid Ligand Binding and Organization on Silica Nanoparticles. Langmuir 2016, 32 (13) , 3253-3261. https://doi.org/10.1021/acs.langmuir.5b03933
    34. Mahdieh Aghamohammadi, Reinhold Rödel, Ute Zschieschang, Carmen Ocal, Hans Boschker, R. Thomas Weitz, Esther Barrena, and Hagen Klauk . Threshold-Voltage Shifts in Organic Transistors Due to Self-Assembled Monolayers at the Dielectric: Evidence for Electronic Coupling and Dipolar Effects. ACS Applied Materials & Interfaces 2015, 7 (41) , 22775-22785. https://doi.org/10.1021/acsami.5b02747
    35. Fatemeh Sadat Minaye Hashemi, Chaiya Prasittichai, and Stacey F. Bent . Self-Correcting Process for High Quality Patterning by Atomic Layer Deposition. ACS Nano 2015, 9 (9) , 8710-8717. https://doi.org/10.1021/acsnano.5b03125
    36. John T. Gaskins, Anuradha Bulusu, Anthony J. Giordano, John C. Duda, Samuel Graham, and Patrick E. Hopkins . Thermal Conductance across Phosphonic Acid Molecules and Interfaces: Ballistic versus Diffusive Vibrational Transport in Molecular Monolayers. The Journal of Physical Chemistry C 2015, 119 (36) , 20931-20939. https://doi.org/10.1021/acs.jpcc.5b05462
    37. Jennifer W. Chan, Yingyue Zhang, and Kathryn E. Uhrich . Amphiphilic Macromolecule Self-Assembled Monolayers Suppress Smooth Muscle Cell Proliferation. Bioconjugate Chemistry 2015, 26 (7) , 1359-1369. https://doi.org/10.1021/acs.bioconjchem.5b00208
    38. Bhavesh Bhartia, Nadav Bacher, Sundaramurthy Jayaraman, Salam Khatib, Jing Song, Shifeng Guo, Cedric Troadec, Sreenivasa Reddy Puniredd, Madapusi Palavedu Srinivasan, and Hossam Haick . Application of Organophosphonic Acids by One-Step Supercritical CO2 on 1D and 2D Semiconductors: Toward Enhanced Electrical and Sensing Performances. ACS Applied Materials & Interfaces 2015, 7 (27) , 14885-14895. https://doi.org/10.1021/acsami.5b03597
    39. Shuyi Liu, Szuheng Ho, Ying Chen, and Franky So . Passivation of Metal Oxide Surfaces for High-Performance Organic and Hybrid Optoelectronic Devices. Chemistry of Materials 2015, 27 (7) , 2532-2539. https://doi.org/10.1021/acs.chemmater.5b00129
    40. Amélie Forget, Benoît Limoges, and Véronique Balland . Efficient Chemisorption of Organophosphorous Redox Probes on Indium Tin Oxide Surfaces under Mild Conditions. Langmuir 2015, 31 (6) , 1931-1940. https://doi.org/10.1021/la503760x
    41. Kyunghun Kim, Tae Kyu An, Jiye Kim, Yong Jin Jeong, Jaeyoung Jang, Haekyung Kim, Jang Yeol Baek, Yun-Hi Kim, Se Hyun Kim, and Chan Eon Park . Grafting Fluorinated Polymer Nanolayer for Advancing the Electrical Stability of Organic Field-Effect Transistors. Chemistry of Materials 2014, 26 (22) , 6467-6476. https://doi.org/10.1021/cm5030266
    42. Melanie Timpel, Marco V. Nardi, Stefan Krause, Giovanni Ligorio, Christos Christodoulou, Luca Pasquali, Angelo Giglia, Johannes Frisch, Berthold Wegner, Paolo Moras, and Norbert Koch . Surface Modification of ZnO(0001)–Zn with Phosphonate-Based Self-Assembled Monolayers: Binding Modes, Orientation, and Work Function. Chemistry of Materials 2014, 26 (17) , 5042-5050. https://doi.org/10.1021/cm502171m
    43. R. Caterino, R. Csiki, M. Wiesinger, M. Sachsenhauser, M. Stutzmann, J. A. Garrido, and A. Cattani-Scholz , Giorgio Speranza , S. D. Janssens and K. Haenen . Organophosphonate Biofunctionalization of Diamond Electrodes. ACS Applied Materials & Interfaces 2014, 6 (16) , 13909-13916. https://doi.org/10.1021/am503305t
    44. Fatemeh Sadat Minaye Hashemi, Chaiya Prasittichai, and Stacey F. Bent . A New Resist for Area Selective Atomic and Molecular Layer Deposition on Metal–Dielectric Patterns. The Journal of Physical Chemistry C 2014, 118 (20) , 10957-10962. https://doi.org/10.1021/jp502669f
    45. Aline Debrassi, Angela Ribbera, Willem M. de Vos, Tom Wennekes, and Han Zuilhof . Stability of (Bio)Functionalized Porous Aluminum Oxide. Langmuir 2014, 30 (5) , 1311-1320. https://doi.org/10.1021/la403525z
    46. He Wang, Enrique D. Gomez, Zelei Guan, Cherno Jaye, Michael F. Toney, Daniel A. Fischer, Antoine Kahn, and Yueh-Lin Loo . Tuning Contact Recombination and Open-Circuit Voltage in Polymer Solar Cells via Self-Assembled Monolayer Adsorption at the Organic–Metal Oxide Interface. The Journal of Physical Chemistry C 2013, 117 (40) , 20474-20484. https://doi.org/10.1021/jp406625e
    47. Fei Hua Li, Jason D. Fabbri, Raisa I. Yurchenko, Alexander N. Mileshkin, J. Nathan Hohman, Hao Yan, Hongyuan Yuan, Ich C. Tran, Trevor M. Willey, Michael Bagge-Hansen, Jeremy E. P. Dahl, Robert M. K. Carlson, Andrey A. Fokin, Peter R. Schreiner, Zhi-Xun Shen, and Nicolas A. Melosh . Covalent Attachment of Diamondoid Phosphonic Acid Dichlorides to Tungsten Oxide Surfaces. Langmuir 2013, 29 (31) , 9790-9797. https://doi.org/10.1021/la401781e
    48. Nico Lämmerhardt, Stephan Merzsch, Johannes Ledig, Achyut Bora, Andreas Waag, Marc Tornow, and Petra Mischnick . Toward Three-Dimensional Microelectronic Systems: Directed Self-Assembly of Silicon Microcubes via DNA Surface Functionalization. Langmuir 2013, 29 (26) , 8410-8416. https://doi.org/10.1021/la401558f
    49. Anuradha Bulusu, Sergio A. Paniagua, Bradley A. MacLeod, Ajaya K. Sigdel, Joseph J. Berry, Dana C. Olson, Seth R. Marder, and Samuel Graham . Efficient Modification of Metal Oxide Surfaces with Phosphonic Acids by Spray Coating. Langmuir 2013, 29 (12) , 3935-3942. https://doi.org/10.1021/la303354t
    50. Kung-Ching Liao, Hafeez Anwar, Ian G. Hill, Grigory K. Vertelov, and Jeffrey Schwartz . Comparative Interface Metrics for Metal-Free Monolayer-Based Dye-Sensitized Solar Cells. ACS Applied Materials & Interfaces 2012, 4 (12) , 6735-6746. https://doi.org/10.1021/am301907z
    51. Peter Thissen, Abraham Vega, Tatiana Peixoto, and Yves J. Chabal . Controlled, Low-Coverage Metal Oxide Activation of Silicon for Organic Functionalization: Unraveling the Phosphonate Bond. Langmuir 2012, 28 (50) , 17494-17505. https://doi.org/10.1021/la3038457
    52. Clémence Queffélec, Marc Petit, Pascal Janvier, D. Andrew Knight, and Bruno Bujoli . Surface Modification Using Phosphonic Acids and Esters. Chemical Reviews 2012, 112 (7) , 3777-3807. https://doi.org/10.1021/cr2004212
    53. Xin Chen, Erwann Luais, Nadim Darwish, Simone Ciampi, Pall Thordarson, and J. Justin Gooding . Studies on the Effect of Solvents on Self-Assembled Monolayers Formed from Organophosphonic Acids on Indium Tin Oxide. Langmuir 2012, 28 (25) , 9487-9495. https://doi.org/10.1021/la3010129
    54. Peter Thissen, Tatiana Peixoto, Roberto C. Longo, Weina Peng, Wolf Gero Schmidt, Kyeongjae Cho, and Yves J. Chabal . Activation of Surface Hydroxyl Groups by Modification of H-Terminated Si(111) Surfaces. Journal of the American Chemical Society 2012, 134 (21) , 8869-8874. https://doi.org/10.1021/ja300270w
    55. Abraham Vega, Peter Thissen, and Yves J. Chabal . Environment-Controlled Tethering by Aggregation and Growth of Phosphonic Acid Monolayers on Silicon Oxide. Langmuir 2012, 28 (21) , 8046-8051. https://doi.org/10.1021/la300709n
    56. Peter J. Hotchkiss, Simon C. Jones, Sergio A. Paniagua, Asha Sharma, Bernard Kippelen, Neal R. Armstrong, and Seth R. Marder . The Modification of Indium Tin Oxide with Phosphonic Acids: Mechanism of Binding, Tuning of Surface Properties, and Potential for Use in Organic Electronic Applications. Accounts of Chemical Research 2012, 45 (3) , 337-346. https://doi.org/10.1021/ar200119g
    57. Jing Shang, Fang Cheng, Manish Dubey, Justin M. Kaplan, Meghana Rawal, Xi Jiang, David S. Newburg, Philip A. Sullivan, Rodrigo B. Andrade, and Daniel M. Ratner . An Organophosphonate Strategy for Functionalizing Silicon Photonic Biosensors. Langmuir 2012, 28 (6) , 3338-3344. https://doi.org/10.1021/la2043153
    58. Igal Levine, Stephanie M. Weber, Yishay Feldman, Tatyana Bendikov, Hagai Cohen, David Cahen, and Ayelet Vilan . Molecular Length, Monolayer Density, and Charge Transport: Lessons from Al–AlOx/Alkyl–Phosphonate/Hg Junctions. Langmuir 2012, 28 (1) , 404-415. https://doi.org/10.1021/la2035664
    59. Jacob Tarver and Yueh-Lin Loo . Mesostructures of Polyaniline Films Affect Polyelectrochromic Switching. Chemistry of Materials 2011, 23 (19) , 4402-4409. https://doi.org/10.1021/cm2023289
    60. Muthukumar Chockalingam, Nadim Darwish, Guillaume Le Saux, and J. Justin Gooding . Importance of the Indium Tin Oxide Substrate on the Quality of Self-Assembled Monolayers Formed from Organophosphonic Acids. Langmuir 2011, 27 (6) , 2545-2552. https://doi.org/10.1021/la104464w
    61. Randall M. Stoltenberg, Chong Liu, and Zhenan Bao . Selective Surface Chemistry Using Alumina Nanoparticles Generated from Block Copolymers. Langmuir 2011, 27 (1) , 445-451. https://doi.org/10.1021/la104094h
    62. David M. Rampulla, Christine M. Wroge, Eric L. Hanson, and James G. Kushmerick . Charge Transport across Phosphonate Monolayers on Indium Tin Oxide. The Journal of Physical Chemistry C 2010, 114 (48) , 20852-20855. https://doi.org/10.1021/jp107209m
    63. Manish Dubey, Tobias Weidner, Lara J. Gamble, and David G. Castner . Structure and Order of Phosphonic Acid-Based Self-Assembled Monolayers on Si(100). Langmuir 2010, 26 (18) , 14747-14754. https://doi.org/10.1021/la1021438
    64. Anke Zeller, Anna Musyanovych, Michael Kappl, Anitha Ethirajan, Martin Dass, Dilyana Markova, Markus Klapper and Katharina Landfester . Nanostructured Coatings by Adhesion of Phosphonated Polystyrene Particles onto Titanium Surface for Implant Material Applications. ACS Applied Materials & Interfaces 2010, 2 (8) , 2421-2428. https://doi.org/10.1021/am1004305
    65. Heng-Yong Nie. Revealing Different Bonding Modes of Self-Assembled Octadecylphosphonic Acid Monolayers on Oxides by Time-of-Flight Secondary Ion Mass Spectrometry: Silicon vs Aluminum. Analytical Chemistry 2010, 82 (8) , 3371-3376. https://doi.org/10.1021/ac100671q
    66. Jacob Tarver, Joung Eun Yoo and Yueh-Lin Loo . Polyaniline Exhibiting Stable and Reversible Switching in the Visible Extending into the Near-IR in Aqueous Media. Chemistry of Materials 2010, 22 (7) , 2333-2340. https://doi.org/10.1021/cm903455w
    67. By Orb Acton, Guy G. Ting, Patrick J. Shamberger, Fumio S. Ohuchi, Hong Ma and Alex K.-Y. Jen . Dielectric Surface-Controlled Low-Voltage Organic Transistors via n-Alkyl Phosphonic Acid Self-Assembled Monolayers on High-k Metal Oxide. ACS Applied Materials & Interfaces 2010, 2 (2) , 511-520. https://doi.org/10.1021/am9007648
    68. Aparna Raman, Rosalynn Quiñones, Lisa Barriger, Rachel Eastman, Arash Parsi and Ellen S. Gawalt. Understanding Organic Film Behavior on Alloy and Metal Oxides. Langmuir 2010, 26 (3) , 1747-1754. https://doi.org/10.1021/la904120s
    69. Hong MaOrb ActonGuy TingJae Won KaHin-Lap YipAlex K.-Y. Jen. Ultrathin Self-Assembled Organophosphonic Acid Monolayers/Metal Oxides Hybrid Dielectrics for Low-Voltage Field-Effect Transistors. 2010, 229-239. https://doi.org/10.1021/bk-2010-1039.ch016
    70. Carlos A. Aguilar, Richard Haight, Anastassios Mavrokefalos, Brian A. Korgel and Shaochen Chen . Probing Electronic Properties of Molecular Engineered Zinc Oxide Nanowires with Photoelectron Spectroscopy. ACS Nano 2009, 3 (10) , 3057-3062. https://doi.org/10.1021/nn900777k
    71. Craig L. Perkins. Molecular Anchors for Self-Assembled Monolayers on ZnO: A Direct Comparison of the Thiol and Phosphonic Acid Moieties. The Journal of Physical Chemistry C 2009, 113 (42) , 18276-18286. https://doi.org/10.1021/jp906013r
    72. G. Lecollinet, N. Delorme, M. Edely, A. Gibaud, J.-F. Bardeau, F. Hindré, F. Boury and D. Portet . Self-Assembled Monolayers of Bisphosphonates: Influence of Side Chain Steric Hindrance. Langmuir 2009, 25 (14) , 7828-7835. https://doi.org/10.1021/la8039576
    73. Regina Luschtinetz, Johannes Frenzel, Theodor Milek and Gotthard Seifert. Adsorption of Phosphonic Acid at the TiO2 Anatase (101) and Rutile (110) Surfaces. The Journal of Physical Chemistry C 2009, 113 (14) , 5730-5740. https://doi.org/10.1021/jp8110343
    74. Guy G. Ting, II, Orb Acton, Hong Ma, Jae Won Ka and Alex K.-Y. Jen . Study on the Formation of Self-Assembled Monolayers on Sol−Gel Processed Hafnium Oxide as Dielectric Layers. Langmuir 2009, 25 (4) , 2140-2147. https://doi.org/10.1021/la802944n
    75. Jacob Tarver, Joung Eun Yoo, T. Joseph Dennes, Jeffrey Schwartz and Yueh-Lin Loo. Polymer Acid Doped Polyaniline Is Electrochemically Stable Beyond pH 9. Chemistry of Materials 2009, 21 (2) , 280-286. https://doi.org/10.1021/cm802314h
    76. Anna Cattani-Scholz, Daniel Pedone, Manish Dubey, Stefan Neppl, Bert Nickel, Peter Feulner, Jeffrey Schwartz, Gerhard Abstreiter and Marc Tornow . Organophosphonate-Based PNA-Functionalization of Silicon Nanowires for Label-Free DNA Detection. ACS Nano 2008, 2 (8) , 1653-1660. https://doi.org/10.1021/nn800136e
    77. Marcello Campione,, Adele Sassella,, Massimo Moret,, Antonio Papagni,, Silvia Trabattoni,, Roland Resel,, Ondrej Lengyel,, Valentina Marcon, and, Guido Raos. Organic−Organic Epitaxy of Incommensurate Systems:  Quaterthiophene on Potassium Hydrogen Phthalate Single Crystals. Journal of the American Chemical Society 2006, 128 (41) , 13378-13387. https://doi.org/10.1021/ja058771w
    78. Heng-Yong Nie,, Mary J. Walzak, and, N. Stewart McIntyre. Delivering Octadecylphosphonic Acid Self-Assembled Monolayers on a Si Wafer and Other Oxide Surfaces. The Journal of Physical Chemistry B 2006, 110 (42) , 21101-21108. https://doi.org/10.1021/jp062811g
    79. Ling Huang,, Yu-Hsu Chang,, Joseph J. Kakkassery, and, Chad A. Mirkin. Dip-Pen Nanolithography of High-Melting-Temperature Molecules. The Journal of Physical Chemistry B 2006, 110 (42) , 20756-20758. https://doi.org/10.1021/jp065404d
    80. Nina Adden,, Lara J. Gamble,, David G. Castner,, Andrea Hoffmann,, Gerhard Gross, and, Henning Menzel. Phosphonic Acid Monolayers for Binding of Bioactive Molecules to Titanium Surfaces. Langmuir 2006, 22 (19) , 8197-8204. https://doi.org/10.1021/la060754c
    81. Eric L. Hanson,, Jing Guo,, Norbert Koch,, Jeffrey Schwartz, and, Steven L. Bernasek. Advanced Surface Modification of Indium Tin Oxide for Improved Charge Injection in Organic Devices. Journal of the American Chemical Society 2005, 127 (28) , 10058-10062. https://doi.org/10.1021/ja050481s
    82. Brett M. Silverman,, Kristen A. Wieghaus, and, Jeffrey Schwartz. Comparative Properties of Siloxane vs Phosphonate Monolayers on A Key Titanium Alloy. Langmuir 2005, 21 (1) , 225-228. https://doi.org/10.1021/la048227l
    83. P. Hubert Mutin,, Vincent Lafond,, Aurelian F. Popa,, Michel Granier,, Laurent Markey, and, Alain Dereux. Selective Surface Modification of SiO2−TiO2 Supports with Phosphonic Acids. Chemistry of Materials 2004, 16 (26) , 5670-5675. https://doi.org/10.1021/cm035367s
    84. Peng Wang,, Cédric Klein,, Jacques-E. Moser,, Robin Humphry-Baker,, Ngoc-Le Cevey-Ha,, Raphael Charvet,, Pascal Comte,, Shaik M. Zakeeruddin, and, Michael Grätzel. Amphiphilic Ruthenium Sensitizer with 4,4‘-Diphosphonic Acid-2,2‘-bipyridine as Anchoring Ligand for Nanocrystalline Dye Sensitized Solar Cells. The Journal of Physical Chemistry B 2004, 108 (45) , 17553-17559. https://doi.org/10.1021/jp046932x
    85. Kim S. Midwood,, Michael D. Carolus,, Michael P. Danahy,, Jean E. Schwarzbauer, and, Jeffrey Schwartz. Easy and Efficient Bonding of Biomolecules to an Oxide Surface of Silicon. Langmuir 2004, 20 (13) , 5501-5505. https://doi.org/10.1021/la049506b
    86. Caoimhe Robinson, Vuslat B. Juska, Alan O'Riordan. Surface chemistry applications and development of immunosensors using electrochemical impedance spectroscopy: A comprehensive review. Environmental Research 2023, 237 , 116877. https://doi.org/10.1016/j.envres.2023.116877
    87. . References. 2023, 185-250. https://doi.org/10.1002/9783527840489.ref
    88. Yanyan Lin, Ningbo Cheng, Na Meng, Chao Wang, Xianfeng Wang, Jianyong Yu, Bin Ding. A Patterned Knitted Fabric with Reversible Gating Stability for Dynamic Moisture Management of Human Body. Advanced Functional Materials 2023, 41 https://doi.org/10.1002/adfm.202304109
    89. Josué Cordero-Guerrero, Gabriel Jiménez-Thuel, Sergio A. Paniagua. Sub-micron patterning of metal oxide surfaces via microcontact printing and microtransfer molding of amphiphilic molecules and antifouling application. Journal of Materials Research 2023, 38 (6) , 1573-1582. https://doi.org/10.1557/s43578-023-00909-x
    90. Lauren S. Puumala, Samantha M. Grist, Jennifer M. Morales, Justin R. Bickford, Lukas Chrostowski, Sudip Shekhar, Karen C. Cheung. Biofunctionalization of Multiplexed Silicon Photonic Biosensors. Biosensors 2023, 13 (1) , 53. https://doi.org/10.3390/bios13010053
    91. Ashwini Kumar, Andrea Perinot, Sudipta Kumar Sarkar, Dipti Gupta, Nicolas F. Zorn, Jana Zaumseil, Mario Caironi. Low-temperature solution-processed high-capacitance AlOx dielectrics for low-voltage carbon-based transistors. Organic Electronics 2022, 110 , 106636. https://doi.org/10.1016/j.orgel.2022.106636
    92. Zane Datson, Essam Dief, Tiexin Li, Anton Le Brun, Nadim Darwish. Electrochemical grafting of organic films on silica. Chemical Communications 2022, 58 (81) , 11378-11381. https://doi.org/10.1039/D2CC03169H
    93. Alexei Goun, Esther Frederick, Ali O. Er, Steven L. Bernasek, Herschel Rabitz. Deprotonation of phenol linked to a silicon dioxide surface using adaptive feedback laser control with a heterodyne detected sum frequency generation signal. Physical Chemistry Chemical Physics 2022, 24 (32) , 19443-19451. https://doi.org/10.1039/D1CP05613A
    94. Sue Woon Tan, Tun Naw Sut, Won-Yong Jeon, Bo Kyeong Yoon, Joshua A. Jackman. On/off switching of lipid bicelle adsorption on titanium oxide controlled by sub-monolayer molecular surface functionalization. Applied Materials Today 2022, 27 , 101444. https://doi.org/10.1016/j.apmt.2022.101444
    95. Ho Jae Shim, Jin Seok Kim, Da Won Ahn, Jin Hyun Choe, Eunsu Jung, Donghyuk Oh, Kyung Soo Kim, Sung Chul Lee, Sung Gyu Pyo. Raman Shift of Surface Reaction and Plasma Induced Surface Damage by TNF3/BNF3 Reactive Ion Etching Process. Electronic Materials Letters 2022, 18 (3) , 321-329. https://doi.org/10.1007/s13391-022-00341-z
    96. Heng-Yong Nie, Hamid-Reza Jahangiri-Famenini. Time-of-Flight Secondary Ion Mass Spectrometry Analyses of Self-Assembled Monolayers of Octadecyltrimethoxysilane on SiO2 Substrate. Applied Sciences 2022, 12 (10) , 4932. https://doi.org/10.3390/app12104932
    97. Sarah Wenderoth, Andreas Eigen, Susanne Wintzheimer, Johannes Prieschl, Andreas Hirsch, Marcus Halik, Karl Mandel. Supraparticles with a Mechanically Triggerable Color‐Change‐Effect to Equip Coatings with the Ability to Report Damage. Small 2022, 18 (15) https://doi.org/10.1002/smll.202107513
    98. Yusuke Ishizaka, Kazuhiro Matsumoto, Kazuhiko Sato, Jun‐Chul Choi. Phosphonate‐Type Pseudo‐Grafted Precursor: Efficient Surface Modification of Silica. Chemistry–Methods 2022, 2 (4) https://doi.org/10.1002/cmtd.202100080
    99. Y. Coffinier, Rabah Boukherroub. Surface modification of silicon nanowires for biosensing. 2022, 25-68. https://doi.org/10.1016/B978-0-12-821351-3.00017-3
    100. Norbert Koch. Opportunities for energy level tuning at inorganic/organic semiconductor interfaces. Applied Physics Letters 2021, 119 (26) https://doi.org/10.1063/5.0074963
    Load more citations
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect