The Novel Diphenylamines - Basic Electroconducting Materials

Joanna Cabaj 1Krzysztof Idzik 1Jadwiga Sołoducho 1Mieczysław Łapkowski 2Sylwia Golba 2

1. Wrocław University of Technology, Department of Chemistry, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland
2. Silesian Technical University, Faculty of Chemistry, M. Strzody 9, Gliwice 41-100, Poland

Abstract

Conjugated polymers semiconductors with high charge carrier mobility air stability are of enormous interest for applications in organic electronics, particularly thin film transistors or photovoltaic cells. Although a large number of structurally diverse π- conjugated polymers have been investigated, only a small number have field effect mobility of holes or electrons.

Nearly all current p-type polymer semiconductors for OFETs with moderate to high hole mobility are poly(3-alkylthiophene)s and various thiophene-containing copolymers, that materials require, most notably good π-electron delocalization along the chain and a high degree of intramolecular order, good intramolecular π-stacking and important, low ionization potential.1

Polymers constructed from diphenylamine building blocks are versatile materials that exhibit a variety of advanced functional properties such as high hole-transporting and light-emitting efficiencies large two-photon absorption cross sections, high photorefractivity and photoconductivity, and large stabilization effect on high-spin polyradicals in organic magnets.2

In this study, a novel series of multi-diphenylamine substituted derivatives bearing an bisarylene as a functional core were synthesized. The key step in this type of synthesis 3 has been the Stille type coupling reaction between the N-alkyldibromodiphenylamine and tin derivatives of arylene as the best way for preparation of conjugated N-alkyldiphenylamine derivatives.

For this group of compounds were also investigated an electrochemical polymerization effect and widely adopted approach to prepare structurally ordered thin, electroconducting films by Langmuir – Blodgett technique.

  1. Zhu, Y., Babel, A., Jenekhe, S. A., Macromolecules, 2005, 38, 7983-7991
  2. Velusamy, M., Justin Thomas, K. R., Lin, J. T., Wen. Y. S., Tetrahedron Lett., 2005,46,7647-7651
  3. Sołoducho J, Idzik K., Cabaj J., Doskocz J., Łapkowski M., Plewa S., ARKIVOC (Gainesville, FL, United States) 2007 (vi) 75-89

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Presentation: Poster at E-MRS Fall Meeting 2007, Symposium B, by Joanna Cabaj
See On-line Journal of E-MRS Fall Meeting 2007

Submitted: 2007-05-14 17:38
Revised:   2009-06-07 00:48
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