[en] In this paper we present a joint experimental and theoretical approach for the study of the assembly of end-substituted oligothiophenes at surfaces with different polarities (i.e., mica vs graphite). Scanning probe microscopy studies of (sub)monolayer deposits show various types of structures (one-dimensional fibrils, two-dimensional regular layers, and monolayers), depending on the nature of the end groups and the substrate. Using molecular modeling with an atomistic approach, we focus on the interplay between the molecule-molecule (and segment-segment) interactions and the molecule-substrate interactions and their influence on the observed morphologies and the stacking geometry. Such information is relevant for controling the structural order in thin layers of thiophene oligomers for use in field-effect transistor applications, for example, by modifying the nature of dielectric material over which those compounds are deposited.
Disciplines :
Chemistry
Author, co-author :
Surin, Mathieu ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Leclère, Philippe ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
De Feyter, S.
Abdel-Mottaleb, M.M.S.
De Schryver, F.C.
Henze, O.
Feast, J.W.
Lazzaroni, Roberto ; Université de Mons > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Language :
English
Title :
Molecule-Molecule versus Molecule-Substrate Interactions in the Assembly of Oligothiophenes at Surfaces
Publication date :
24 November 2006
Journal title :
Journal of Physical Chemistry B
ISSN :
1520-6106
Publisher :
American Chemical Society, United States - District of Columbia
Volume :
110
Issue :
15
Pages :
7898-7908
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S817 - Chimie des matériaux nouveaux
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
(c) Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. N.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Nature 1999, 401, 685.
Leclère, Ph.; Surin, M.; Viville, P.; Lazzaroni, R.; Kilbinger, A. F. M.; Henze, O.; Feast, W. J.; Cavallini, M.; Biscarini, F.; Schenning, A. P. H. J.; Meijer, E. W. Chem. Mater. 2004, 16, 4452.
For oligothiophene assembly on different substrates, see: (a) Lang, P.; Ardhaoui, M. E.; Wittmann, J. C.; Dallas, J. P.; Horowitz, G.; Lotz, B.; Gamier, F.; Strupe, C. Synth. Met. 1997, 84, 605.
(b) Prato, S.; Floreano, L.; Cvetko, D.; De Renzi, V.; Morgante, A.; Modesti, S.; Biscarini, F.; Zamboni, R.; Taliani, C. J. Phys. Chem. B 1999, 103, 7788.
(c) Azumi, R.; Götz, G.; Debaerdemaeker, T.; Bäuerle; P. Chem. - Eur. J. 2000, 6, 735.
(d) Chang, P. C.; Lee, J.; Huang, D., Subramanian, V.; Murphy, A. R.; Fréchet, J. M. J. Chem. Mater. 2004, 16, 4783.
For a review on the structural order in pentacene layers, see: Ruiz, R.; Choudhary, D.; Nickel, B.; Toccoli, T.; Chang, K.-C.; Mayer, A. C.; Clancy, P.; Blakely, J. M.; Headrick, R. L.; Iannotta, S.; Malliaras, G. M. Chem. Mater. 2004, 16, 4497.
(b) Wang, G.; Moses, D.; Heeger, A. J.; Zhang, H.-M.; Narasimhan, M.; Demaray, R. E. J. Appl. Phys. 2004, 95, 316.
Zangh, Y.; Lu, R.; Liu, Q.; Song, Y.; Jiang, L.; Liu, Y.; Zhao, Y.; Li, T. J. Thin Solid Films 2003, 437, 150.
Henze, O.; Parker, D.; Feast, W. J. J. Mater. Chem. 2003, 13, 1269.
(a) Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
(b) Casewit, C. J.; Colwell, K. S.; Rappé, A. K. J. Am. Chem. Soc. 1992, 114, 10035
(c) Casewit, C. J.; Colwell, K. S.; Rappé, A. K. J. Am. Chem. Soc. 1992, 114, 10046.
Gaudel-Siri, A.; Brocorens, P.; Siri, D.; Gardebien, F.; Brédas, J. L.; Lazzaroni, R. Langmuir 2003, 19, 8287.
Brigatti, M. C.; Frigieri, P.; Poppi, L. Am. Mineral. 1998, 83, 775.
Greathouse, J. A.; Refson, K.; Sposito, G. J. Am. Chem. Soc. 2000, 122, 11459.
(a) Müller, K.; Chang C. C. Surf. Sci. 1969, 14, 39.
(b) Campbell, P. A.; Sinnamon, L. J.; Thompson C. E.; Walmsley D. G. Surf. Sci. 1998, 410, 768.
Odelius, M.; Bernasconi, M.; Parinello, M. Phys. Rev. Lett.1997, 78, 2855.
The crystallographic parameters of graphite are from: McKie, D.; McKie, C. Essentials of Crystallography; Blackwell Scientific Publications: Boston, 1986.
Biscarini, F.; Zamboni, R.; Samori, P.; Ostoja, P.; Taliani, C. Phys. Rev. B 1995, 52, 14868.
Barabási A.-L. and Stanley, H. E. Fractal Concepts in Surface Growth; Cambridge University Press: Cambridge, U. K., 1995.
Schenning, A. P. H. J.; Kilbinger, A. F. M.; Biscarini, F.; Cavallini, M.; Cooper, H. J.; Derrick, P. J., Feast, W. J.; Lazzaroni, R.; Leclère, Ph.; McDonell, L. A.; Meijer, E. W.; Meskers, S. C. J. J. Am. Chem. Soc. 2002, 124, 1269.
De Feyter, S.; De Schryver, F. C. Chem. Soc. Rev. 2003, 32, 139.
Lazzaroni, R.; Calderone, A.; Brédas, J. L.; Rabe, J. P. J. Chem. Phys. 1997, 107, 99.
Stabel, A.; Rabe, J. P. Synth. Met. 1994, 67, 47.
The RDF is the spherically averaged distribution of interatomic distances during the MD run.
Rabe, G. W.; Heise, H.; Liable-Sands, L. M.; Guzei, I. A.; Rheingold, A. L. J. Chem. Soc., Dalton Trans. 2000, 1863.
Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
(a) Buchholz, S.; Rabe, J. P. Angew. Chem., Int. Ed. Engl. 1992, 31, 189.
(b) Arnold, T.; Thomas, R. K.; Castro, M. A.; Clarke, S. M.; Messe, L.; Inaba, A. Phys. Chem. Chem. Phys. 2002, 4, 345.
(a) Paserba, K.; Gellman, A. J. Phys. Rev. Lett. 2001, 86, 4338.
(b) Gellman, A. J.; Paserba, K. P. J. Phys. Chem. B 2002, 106, 13231.
Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318.
In the layered islands of (EO)5-T6-Hex on mica, the estimated binding energy between a stack of 18 molecules in a layer and a single molecule in the layer on top, i.e., Eb,M-M between layers, is around 20 kJ/ mol.
Sandberg, H. G. O.; Henze, O.; Sirringhaus, H.; Kilbinger, A.; Feast, W. J.; Friend, R. H. Proc. SPIE - Int. Soc. Opt. Eng. 2001, 4466, 35.