Single and Mixed Self-Assembled Monolayers of Phenyl Species on SiO2 with Various Ring to Ring Interactions


We studied the formation of phenylalkyltrichlorosilane self-assembled monolayers on native oxide covered silicon. After a first chemisorption step in the monolayer growth, the presence of the short alkyl chain (3-4 carbon atoms) is responsible for a second growth step which corresponds to the arrangement between molecules. We found that this packing step is accelerated by replacing phenyl by pentafluoro-phenyl rings, possibly due to quadrupolar interactions between fluorinated cycles. Furthermore we demonstrate that mixing phenyl and pentafluoro-phenyl molecules leads to an even faster packing step which is accounted for by hydrogen bonding CH...FC in a face to face phenyl/pentafluoro-phenyl arrangement. We believe these results allow improving charge delocalization over conjugated molecular domains. In a second part, we studied the phase separation between phenyl-alkyltrichlorosilane and octadecyltrichlorosilane (OTS) molecules. Improving the phase separation was studied using ring to ring interactions afore-analyzed. We show phase separation is improved and OTS islands are smaller with phenyl species that involve stronger ring to ring interactions. The best case is obtained with mixing phenyl and pentafluoro-phenyl rings using hydrogen bonds for packing together the aromatic species. These results demonstrate improved control of SAM composition and morphology essential to further use the obtained islands for building molecular devices.

This is a preview of subscription content, access via your institution.


  1. 1

    G.M. Whitesides, B. Grzybowski, Science 295, 2418 (2002).

    CAS  Article  Google Scholar 

  2. 2

    A. Ulman, An introduction to ultrathin organic films (Academic Press: Boston, 1991)

    Google Scholar 

  3. 3

    M. Halik, H. Klauk, U. Zschieschang, G. Schmid, C. Dehm, M. Schütz, S. Maisch, F. Effenberger, M. Brunnbauer, F. Stellacci, Nature 431, 963 (2004)

    CAS  Article  Google Scholar 

  4. 4

    F. Fan, C. Maldarelli, A. Couzis, Langmuir 19, 3254 (2003)

    CAS  Article  Google Scholar 

  5. 5

    J. Collet, S. Lenfant, D. Vuillaume, O. Bouloussa, F. Ro,delez, J.M. Gay, K. Kham, C. Chevrot, Appl. Phys. Lett. 76, 1339 (2000)

    CAS  Article  Google Scholar 

  6. 6

    J.D. Dunitz, ChemBioChem 5, 614 (2004)

    CAS  Article  Google Scholar 

  7. 7

    J. Moineau, M. Granier, G.F. Lanneau, Langmuir 20, 3202 (2004).

    CAS  Article  Google Scholar 

  8. 8

    E.A. Meyer, R.K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42, 1210 (2003)

    CAS  Article  Google Scholar 

  9. 9

    C. Carraro, O.W. Yauw, MM. Sung, R. Maboudian, J. Phys. Chem. B 102, 4441 (1998)

    CAS  Article  Google Scholar 

  10. 10

    C.D. Bain, G.M. Whitesides, J. Am. Chem. Soc. 111, 7164 (1989)

    CAS  Article  Google Scholar 

  11. 11

    A.B.D. Cassie, S. Baxter, Trans. Faraday Soc. 40, 546 (1944)

    CAS  Article  Google Scholar 

  12. 12

    Software WSxM from Nanotec Electronica, freeware

  13. 13

    S. Desbief, L. Patrone, D. Goguenheim, D. Guerin, D. Vuillaume, (submitted)

  14. 14

    V.R. Thalladi et al., J.Am.Chem.Soc. 120, 8702 (1998)

    CAS  Article  Google Scholar 

  15. 15

    S. Zhu, S. Zhu, G. Jin, Z. Li, Tetrahedr. Lett. 46, 2713 (2005)

    CAS  Article  Google Scholar 

  16. 16

    Brzoska, J.B.; Ben Azouz, I.; Rondelez, F. Langmuir 10, 4367 (1994)

    CAS  Article  Google Scholar 

  17. 17

    W. Mizutani, T. Ishida, S.I. Yamamoto, H. Tokumoto, H. Hokari, H. Azehara, M. Fujihira Appl. Phys. A 66, S1257–S1260 (1998)

    CAS  Article  Google Scholar 

Download references

Author information



Corresponding author

Correspondence to Virginie Gadenne.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Gadenne, V., Patrone, L. & Desbief, S. Single and Mixed Self-Assembled Monolayers of Phenyl Species on SiO2 with Various Ring to Ring Interactions. MRS Online Proceedings Library 1154, 523 (2008).

Download citation