Novel conjugated nanomaterials based on pyrimidine structures - synthesis and physicochemical profile

Joanna Cabaj 2Jadwiga, Maria Sołoducho 1,2Antoni Chyla 2Krzysztof Idzik 2

1. Wrocław University of Technology, Wybrzeże Wyspiańskiego, Wrocław 50-370, Poland
2. Wrocław University of Technology, Department of Chemistry, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland

Abstract

A great deal of research around the world has been focused on developing novel materials composed of conjugated, self - assembled and saturated units. Conjugated polymers such as polypyrroles, polyphenylenes, polythiophenes have been extensively studied, and many important electrical and optical properties have been discovered [1]. Consequently, there is an apparent attention in the preparation and purification of these materials.

Our considerable interest in precursors of conducting polymers chemistry stimulated us to obtain several, novel symmetric oligoheterocycles. According to continuation previous effects [2], here is reported on the synthesis and certain physicochemical profile of symmetric bis-thiophene or bis-ethylenedioxythiophene derivatives based on pyrimidine.

An interesting results have been obtained by starting from chalcones. Obviously, in our case, after reaction of chalcones with proper amidines we isolated bis(halogenephenyl)pyrimidines. Applying variation of standard Stille procedure for the synthesis C-C coupling products, in the next step bis(phenyl)pyrimidine derivatives were condensed with 2-(trimethylthin)thiophene to get the final compound – 2-alkyl-4,6-bis[4-(2-thiophene)]pyrimidine. Similar results have been achieved by performing the coupling reaction between 2-trimethylthin-3,4-ethylenedioxythiophene with bis(halogenophenyl)pyrimidines.

As it comes from aggregation experiments some pyrimidine derivatives give stable and good quality Langmuir and Langmuir-Blodgett films (in binary systems with docosanoic acid and octadecylthiophene) of desired composition and their electrical properties are currently under investigation.

[1] Pinnavaia T. J., Beali G. W., (Eds.), Polymer-Clay Nanocomposites, New York, John Wiley&Sons, 2000.

[2] Sołoducho J., Doskocz J., Cabaj J., Roszak S., Tetrahedron, 2003, 59, 4761-4766.

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Presentation: poster at E-MRS Fall Meeting 2005, Symposium E, by Joanna Cabaj
See On-line Journal of E-MRS Fall Meeting 2005

Submitted: 2005-05-19 19:51
Revised:   2009-06-07 00:48
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