Hostname: page-component-7c8c6479df-xxrs7 Total loading time: 0 Render date: 2024-03-29T15:52:51.468Z Has data issue: false hasContentIssue false

Electrochemical cross-linking of carbazole derivatives: a new route for bulk heterojunction based on semi-interpenetrating polymer networks*

Published online by Cambridge University Press:  14 February 2007

F. Tran-Van
Affiliation:
Laboratoire de Physico-Chimie des Polymères et des Interfaces, Université de Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France
T.-X. Lav
Affiliation:
Laboratoire de Physico-Chimie des Polymères et des Interfaces, Université de Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France
C. Chevrot*
Affiliation:
Laboratoire de Physico-Chimie des Polymères et des Interfaces, Université de Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France
D. Teyssié
Affiliation:
Laboratoire de Physico-Chimie des Polymères et des Interfaces, Université de Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France
F. Vidal
Affiliation:
Laboratoire de Physico-Chimie des Polymères et des Interfaces, Université de Cergy-Pontoise, 5 mail Gay-Lussac, 95031 Cergy-Pontoise Cedex, France
V. Getautis
Affiliation:
Faculty of Chemical Technology, Kaunas University of Technology, Radvilenu Plentas 19, 3028 Kaunas, Lithuania
J. V. Grazulevicius
Affiliation:
Faculty of Chemical Technology, Kaunas University of Technology, Radvilenu Plentas 19, 3028 Kaunas, Lithuania
Get access

Abstract

Electrochemical behaviors of different pendant carbazole based oligomers have been studied for the realization of electroactive tridimensional structures. 3-substitution by hydrazone functional groups onto the pendant carbazole moieties increases the electron donor properties of the electroactive units. Electrochemical oxidation of thin films of the oligomer precursors deposited onto electrode ensures the formation of a cross-linked structure by in situ anodic coupling with the formation of biscarbazole redox sites. When the electrochemical cross-linking of the oligomers is realized in the presence of the electron acceptor polyimide (perylene based), we form a semi-interpenetrating polymer network (semi-IPN) coated as a thin layer. The electrochemical behavior of the semi-IPN shows two reversible oxidations and two reversible reduction peaks indicating respectively the p-doping of the biscarbazole entity and the n-doping of the perylene one. The presence of hydrazone substituents modifies the electron donor properties of the semi-IPN and should influence the electron transfer properties from biscarbazole to perylene units in bulk heterojunction solar cells.

Keywords

Type
Research Article
Copyright
© EDP Sciences, 2007

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Footnotes

*

This paper has been presented at “ECHOS06”, Paris, 28–30 juin 2006.

References

Shaheen, S.E., Brabec, C.J., Sariciftci, N.S., Padinger, F., Fromherz, T., Appl. Phys. Lett. 78, 841 (2001) CrossRef
Martens, T., Beelen, Z., D'Haen, J., Munters, T., Goris, L., Manca, J., D'Olieslaeger, M., Vanderzande, D., De Schepper, L., Andriessen, R., Synthetic Met. 138, 243 (2003) CrossRef
Reyes-Reyes, M., Kim, K., Carroll, D.L., Appl. Phys. Lett. 87, 083506 (2005) CrossRef
Ma, W., Yang, C., Gong, X., Lee, K., Heeger, A.J., Adv. Funct. Mater. 15, 1617 (2005) CrossRef
Yang, X., Loos, J., Veenstra, S.C., Verhees, W.J.H., Wienk, M.M., Kroon, J.M., Michels, M.A.J., Janssen, R.A.J., Nano Lett. 5, 579 (2005) CrossRef
U. Zhokhavets, T. Erb, H. Hoppe, G. Gobsch N.S. Sariciftci, Thin Solid Films 496, 679 ( 2006)
Hoppe, H., Sariciftci, N.S., J. Mater. Chem. 16, 45 (2006) CrossRef
Reyes-Reyes, M., Kim, K., Dewald, J., López-Sandoval, R., Avadhanula, A., Curran, S., Carroll, D.L., Org. Lett. 7, 5749 (2005) CrossRef
Jensen, B.W., West, K., Synthetic Met. 148, 105 (2005) CrossRef
Oh, S.-W., Rhee, H.W., Kim, Y.C., Kim, J.K., Yu, J.-W., Current Appl. Phys. 6, 739 (2006) CrossRef
Deng, S., Advincula, R.C., Chem. Mater. 14, 4073 (2002) CrossRef
Taranekar, P., Fan, X., Advincula, R., Langmuir 18, 7943 (2002) CrossRef
Xia, C., Fan, X., Park, M., Advincula, R.C., Langmuir 17, 7893 (2001) CrossRef
Inaoka, S., Advincula, R., Macromolecules 35, 2426 (2002) CrossRef
Xia, C., Advincula, R.C., Baba, A., Knoll, W., Chem. Mater. 16, 2852 (2004) CrossRef
Baba, A., Onishi, K., Knoll, W., Advincula, R.C., J. Phys. Chem. B 108, 18949 (2004) CrossRef
Taranekar, P., Baba, A., Fulghum, M., Advincula, R., Macromolecules 38, 3679 (2005) CrossRef
Michot, C., Baril, D., Armand, M., Sol. Energ. Mat. Sol. C. 39, 289 (1995) CrossRef
Williams, M.E., Murray, R.W., Chem. Mater. 10, 3603 (1998) CrossRef
Buika, G., Grazulevicius, J.V., Eur. Polym. J. 29, 1489 (1993) CrossRef
J. Nusrallah, Z. Tokarski, V. Getautis, J.V. Grazulevicius, I. Paulauskaite, J.A. Reina, V. Gaidelis, V. Jankauskas, European Patent Application EP 1 584 987 A2 (2005)
Chen, Z., Debije, M.G., Debaerdemaeker, T., Osswald, P., Würthner, F., Chem. Phys. Chem. 5, 137 (2004)
Ostrauskaite, J., Voska, V., Antulis, J., Gaidelis, V., Jankauskas, V., Grazulevicius, J.V., J. Mater. Chem. 12, 3469 (2002) CrossRef
Ambrose, J.F., Nelson, R.F., J. Electrochem. Soc. 115, 1159 (1968) CrossRef
Ambrose, J.F., Carpenter, L.L., Nelson, R.F., J. Electrochem. Soc. 122, 876 (1975) CrossRef
M. Armand, J.M. Chabagnot, M. Duclot, Fast ion transport in solids, edited by P. Vahista, J.N. Mundy, G.K. Shenoy (North-Holland, Amsterdam, 1979), Vol. 131
Russel, D., Meyer, R., Jubran, N., Tokarski, Z., Moudry, R., Law, K., J. Electroanal. Chem. 19, 567 (2004)
Cervini, R., Li, X.-C., Spencer, G.W.C., Holmes, A.B., Moratti, S.C., Friend, R.H., Synthetic Met. 84, 359 (1997) CrossRef
Shin, W.S., Jeong, H.H., Kim, M.K., Jin, S.H., Kim, M.R., Lee, J.K., Lee, J.W., Gal, Y.S., J. Mater. Chem. 16, 384 (2006) CrossRef
Bredas, J.L., Beljonne, D., Coropceanu, V., Cornil, J., Chem. Rev. 104, 4917 (2004) CrossRef
Scharber, M.C., Mühlbacher, D., Koppe, M., Denk, P., Waldauf, C., Heeger, A.J., Brabec, C.J., Adv. Mater. 18, 789 (2006) CrossRef