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

Geng, Yan; Pfattner, Raphael; Campos, Antonio; Wang, Wei; Jeannin, Olivier; Hauser, Jürg; Puigdollers, Joaquim; Bromley, Stefan T.; Decurtins, Silvio; Veciana, Jaume; Rovira, Concepció; Mas-Torrent, Marta; Liu, Shi-Xia (2014). HOMO Stabilisation in π-Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field-Effect Transistors. Chemistry - a European journal, 20(50), pp. 16672-16679. Wiley-VCH 10.1002/chem.201404508

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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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