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HOMO Stabilisation in π-Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field-Effect Transistors

ChemEurJ2014

Dr. Yan Geng, Dr. Raphael Pfattner, Antonio Campos, Prof. Wei Wang, Dr. Olivier Jeannin, Dr. Jürg Hauser, Dr. Joaquim Puigdollers, Prof. Stefan T. Bromley, Prof. Silvio Decurtins, Prof. Jaume Veciana, Prof. Concepció Rovira, Dr. Marta Mas-Torrent* and Dr. Shi-Xia Liu* .

Chemistry - A European Journal, Volume 20Issue 50pages 16672–16679December 8, 2014

 

Three new organic semiconductors, in which either two methoxy units are directly linked to a dibenzotetrathiafulvalene (DB-TTF) central core and a 2,1,3-chalcogendiazole is fused on the one side, or four methoxy groups are linked to the DB-TTF, have been synthesised as active materials for organic field-effect transistors (OFETs). Their electrochemical behaviour, electronic absorption and fluorescence emission as well as photoinduced intramolecular charge transfer were studied. The electron-withdrawing 2,1,3-chalcogendiazole unit significantly affects the electronic properties of these semiconductors, lowering both the HOMO and LUMO energy levels and hence increasing the stability of the semiconducting material. The solution-processed single-crystal transistors exhibit high performance with a hole mobility up to 0.04 cm2 V−1 s−1 as well as good ambient stability.

 

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