Formation of an Atomically Abrupt Interface between a Polycyclic Aromatic Molecule and the Silicon (001) Surface via Direct Si−C LinkageClick to copy article linkArticle link copied!
Abstract
The reaction of acenaphthylene with the Si(001) surface has been investigated as a model system for understanding how complex π-systems interact with a π-bonded semiconductor surface. Scanning tunneling microscopy (STM) reveals that bonding occurs over a dimer row for more than 90% of the adsorbed molecules. Fourier transform infrared spectroscopy (FTIR), using isotopically labeled derivatives of acenaphthylene, shows that bonding occurs through the 1,2-alkene, leaving the aromatic portion of the molecule mostly unperturbed. The reaction between acenaphthylene and Si(001) represents a potential method for coupling extended π-electron systems with group IV semiconductor surfaces.
*
Corresponding author. Phone: 608-262-6371. Fax: 608-262-0453. E-mail: [email protected].
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 18 publications.
- Feng Tao, Steven L. Bernasek and Guo-Qin Xu . Electronic and Structural Factors in Modification and Functionalization of Clean and Passivated Semiconductor Surfaces with Aromatic Systems. Chemical Reviews 2009, 109
(9)
, 3991-4024. https://doi.org/10.1021/cr8003532
- Timothy R. Leftwich and, Andrew V. Teplyakov. Cycloaddition Reactions of Phenylazide and Benzylazide on a Si(100)-2 × 1 Surface. The Journal of Physical Chemistry C 2008, 112
(11)
, 4297-4303. https://doi.org/10.1021/jp711367s
- Solomon Ssenyange,, Franklin Anariba,, David F. Bocian, and, Richard L. McCreery. Covalent Bonding of Alkene and Alkyne Reagents to Graphitic Carbon Surfaces. Langmuir 2005, 21
(24)
, 11105-11112. https://doi.org/10.1021/la0516173
- Richard L. McCreery. Molecular Electronic Junctions. Chemistry of Materials 2004, 16
(23)
, 4477-4496. https://doi.org/10.1021/cm049517q
- F. J. Himpsel,, J. L. McChesney,, J. N. Crain,, A. Kirakosian,, V. Pérez-Dieste,, Nicholas L. Abbott,, Yan-Yeung Luk,, Paul F. Nealey, and, Dmitri Y. Petrovykh. Stepped Silicon Surfaces as Templates for One-Dimensional Nanostructures. The Journal of Physical Chemistry B 2004, 108
(38)
, 14484-14490. https://doi.org/10.1021/jp049209f
- Francesca Nunzi and, Antonio Sgamellotti, , Nazzareno Re. Density Functional Study on the Interaction of a Polycyclic Aromatic Molecule and the Silicon (001) Surface. The Journal of Physical Chemistry B 2004, 108
(30)
, 10881-10886. https://doi.org/10.1021/jp048914l
- Kevin P. Weidkamp,, Christina A. Hacker,, Michael P. Schwartz,, Xiaoping Cao,, Rudolf M. Tromp, and, Robert J. Hamers. Interfacial Chemistry of Pentacene on Clean and Chemically Modified Silicon (001) Surfaces. The Journal of Physical Chemistry B 2003, 107
(40)
, 11142-11148. https://doi.org/10.1021/jp035385x
- I. A. Opeida, Yu. E. Litvinov, O. V. Kushch, M. A. Kompanets, A. N. Shendrik, A. G. Matvienko, A. A. Novokhatko. Rate constants and isotope effects for the reaction of H-atom abstraction from RH substrates by PINO radicals. Russian Journal of Physical Chemistry A 2016, 90
(11)
, 2142-2149. https://doi.org/10.1134/S0036024416110194
- I. O. Opeida, Yu. E. Litvinov, O. V. Kushch, M. O. Kompanets, O. M. Shendrik. Kinetic Studies of Acenaphthene Oxidation Catalyzed by
N
‐Hydroxyphthalimide. International Journal of Chemical Kinetics 2013, 45
(8)
, 515-524. https://doi.org/10.1002/kin.20790
- Andrew V. Teplyakov. Influence of Functional Groups in Substituted Aromatic Molecules on the Selection of Reaction Channel in Semiconductor Surface Functionalization. 2012, 105-161. https://doi.org/10.1002/9781118199770.ch6
- Kian Soon Yong, Guo‐Qin Xu. Covalent Binding of Polycyclic Aromatic Hydrocarbon Systems. 2012, 163-191. https://doi.org/10.1002/9781118199770.ch7
- Robert J. Hamers. Formation and Characterization of Organic Monolayers on Semiconductor Surfaces. Annual Review of Analytical Chemistry 2008, 1
(1)
, 707-736. https://doi.org/10.1146/annurev.anchem.1.031207.112916
- PEIJI ZHAO, DWIGHT WOOLARD, JORGE M. SEMINARIO, ROBERT TREW. TOWARDS SENSING SINGLE OR A FEW BIO-MOLECULAR ARCHITECTURES: DESIGN OF FUNCTIONAL SURFACES. International Journal of High Speed Electronics and Systems 2008, 18
(01)
, 187-194. https://doi.org/10.1142/S0129156408005266
- Peiji Zhao, Dwight Woolard. Electrostatic characteristics of tether atoms in connecting organic molecules to the surface of silicon. Applied Physics Letters 2007, 91
(6)
https://doi.org/10.1063/1.2766670
- PEIJI ZHAO, DWIGHT WOOLARD, JORGE M. SEMINARIO, ROBERT TREW. MIXED-VALENCE TRANSITION METAL COMPLEX BASED INTEGRAL ARCHITECTURE FOR MOLECULAR COMPUTING (I): ATTACHMENT OF LINKER MOLECULE TO SILICON (100) - 2×1 SURFACE. International Journal of High Speed Electronics and Systems 2006, 16
(02)
, 705-712. https://doi.org/10.1142/S0129156406003953
- T. Soubiron, F. Vaurette, J.P. Nys, B. Grandidier, X. Wallart, D. Stiévenard. Molecular interactions of PTCDA on Si(100). Surface Science 2005, 581
(2-3)
, 178-188. https://doi.org/10.1016/j.susc.2005.02.050
- Semyon Bocharov, Andrew V. Teplyakov. Adsorption, ordering, and chemistry of nitrobenzene on Si(100)-2×1. Surface Science 2004, 573
(3)
, 403-412. https://doi.org/10.1016/j.susc.2004.09.044
- Yuniarto Widjaja, Charles B. Musgrave. Indirect adsorbate–adsorbate interactions mediated through the surface electronic structure of the Si(100) surface. The Journal of Chemical Physics 2004, 120
(3)
, 1555-1559. https://doi.org/10.1063/1.1631932
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.