Improved Synthesis of the High-Mobility Organic Semiconductor Dithio­phene-Tetrathiafulvalene

Abstract

Dithiophene-tetrathiafulvalene (DT-TTF) has been shown to be a promising organic semiconductor for organic transistors, since it combines high mobility with processability. A novel synthesis to prepare this material is described here. It involves the coupling of a 1,3-dithiol-2-one. The yield of this route is higher than previously reported yields.

Key words

tetrathiafulvalene - 1,3-dithiol-2-one - coupling reactions - cyclizations - sulfur heterocycles

References

• 1 Ferraris J. Cowan DO. Walatka V. Pelstein JH. J. Am. Chem. Soc.  1973,  95:  948 
• 2a Williams JM. Ferrano JR. Carlson KD. Geiser U. Wang HH. Kini AM. Whango MH. Organic Superconductors (Including Fullerenes); Synthesis, Structure, Properties and Theory   Prentice Hall; New Jersey: 1992. 
• 2b Ishiguro T. Yamaji K. Saito G. Organic Superconductors   2nd ed., Vol. 88:  Springer Series in Solid State Sciences, Springer; Berlin: 1998. 
• 2c Adam M. Müllen K. Adv. Mater.  1994,  6:  439 
• 2d Graja A. Low Dimensional Organic Conductors   World Scientific Publishing; Singapore: 1992. 
• 2e Schukat G. Fanghänel E. Sulfur Rep.  2003,  24:  1 
• 3 Yamada J.-I. Sugimoto T. TTF Chemistry Fundamentals and Applications of Tetrathiafulvalene   Kodansha; Tokyo: Springer; Heidelberg: 2005. 
• 4a Mas-Torrent M. Rovira C. J. Mater. Chem.  2006,  16:  433 
• 4b Mas-Torrent M. Hadley P. Bromley ST. Ribas X. Tarres J. Mas M. Molins E. Veciana J. Rovira C. J. Am. Chem. Soc.  2004,  126:  8546 
• 4c Miskiewicz P. Mas-Torrent M. Jung J. Kotarba S. Glowacki I. Gomar-Nadal E. Amabilino DB. Veciana J. Krause B. Carbone D. Rovira C. Ulanski J. Chem. Mater.  2006,  18:  4274 
• 4d Naraso Nishida J. Kumaki D. Tokio S. Yamashita Y. J. Am. Chem. Soc.  2006,  128:  2750 
• 4e Gao XK. Wu WP. Liu YQ. Qiu WF. Sun XB. Yu G. Zhu DB. Chem. Commun.  2006,  2750 
• 4f Noda B. Katsuhura M. Aoyagi I. Mori T. Taguchi T. Chem. Lett.  2005,  34:  392 
• 5a Mas-Torrent M. Durkut M. Hadley P. Rovira C. J. Am. Chem. Soc.  2004,  126:  984 
• 5b Mas-Torrent M. Hadley P. Bromley ST. Crivillers N. Veciana J. Rovira C. Appl. Phys. Lett.  2005,  86:  12110 
• 6 Rovira C. Veciana J. Santaló N. Tarrés J. Cirujeda J. Molins E. Llorca J. Espinosa E. J. Org. Chem.  1994,  59:  3307 
• 7 Long-Yong C. Shu P. Holt D. Cowan D. J. Org. Chem.  1983,  48:  4713 
• 8 Crivillers N, Oxtoby NS, Mas-Torrent M, Veciana J, and Rovira C. inventors; Patent Application ES  200602663. 
• 9a Dautel OJ. Fourmigué M. J. Org. Chem.  2000,  65:  6479 
• 9b Perez-Benitez A. Tarrés J. Ribera E. Veciana J. Rovira C. Synthesis  1999,  577 
• 9c Ribera E. Veciana J. Molins E. Mata I. Wurst K. Rovira C. Eur. J. Org. Chem.  2000,  2867 
• 10 Larsen J. Lenoir C. Synthesis  1989,  134 
• 11 Stueber D. Patterson D. Mayne CL. Orendt AM. Grant DM. Parry RW. Inorg. Chem.  2001,  40:  1902 
• 12 Ferraris JP. Poehler TO. Bloch AN. Cowan DO. Tetrahedron Lett.  1973,  2553 
• 13a Renner RM. Burns GR. Tetrahedron Lett.  1994,  35:  269 
• 13b Hudhomme P. Le Moustarder S. Durand C. Gallego-Planas N. Mercier N. Blanchard P. Levillain E. Allain M. Gorgues A. Riou A. Chem. Eur. J.  2001,  7:  5070 
• 14 Skabara PJ. Müllen K. Bryce MR. Howard JAK. Batsanov AS. J. Mater. Chem.  1998,  8:  1719