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Synthesis of innovative organic semiconductors based on functionalized tetracenes and derivatives of rubrene (TETRA-FUN)
Start date: Jun 1, 2009, End date: May 31, 2011 PROJECT  FINISHED 

"Organic semiconductors represent a real alternative to inorganic semiconductors for many applications, since they present some evident advantages: are lighter, cheaper, compatible with large area, flexible devices. One of the most promising molecular organic semiconductor is rubrene (5,6,11,12-tetra-phenyl-tetracene); single crystals of rubrene showed hole mobility comparable with that of amorphous silicon. Chemists’ contribution to the research on rubrene can allow to overcome some problems still affecting this promising molecule, namely the tendency to be oxidized, the difficulty to grow crystalline thin films and the lacking of n-type homologues. Objective of this project is the synthesis of new derivatives of tetracene, homologues of rubrene, and the study of their optical and electronic properties, both at molecular and crystal level, and the comparison with rubrene, to learn about the effect of different substituents on structure and properties. The project is aimed therefore to study how different substituents and different supramolecular arrangements can influence charge transport and light emission in the solid state. 5,6,11,12-tetra-aryl-tetracene (rubrene) and homologues can be prepared starting from appropriate 1,1-diphenyl-propargyl alcohols. The first step will be the investigation of the synthesis of tri-aryl-propargyl alcohols and the synthesis of new derivatives. These compounds will be used to prepare the corresponding homologues of rubrene, optimizing the reaction conditions and studying the reaction into the details. These compounds will be the starting point to growth crystalline materials; the main target for the characterization of these materials will be the analyses of the electric properties of these materials. Part of the characterization work will devoted also to the analysis of the structure and of the optical properties (in the UV-visible range) of these materials"
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