Coupling Tetracyanoquinodimethane to Tetrathiafulvalene: A Fused TCNQ–TTF–TCNQ Triad†
Dr. Francisco Otón
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. Vega Lloveras
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. Marta Mas-Torrent
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. José Vidal-Gancedo
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorProf. Jaume Veciana
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorCorresponding Author
Prof. Concepció Rovira
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)Search for more papers by this authorDr. Francisco Otón
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. Vega Lloveras
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. Marta Mas-Torrent
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorDr. José Vidal-Gancedo
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorProf. Jaume Veciana
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Search for more papers by this authorCorresponding Author
Prof. Concepció Rovira
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)
Molecular Nanoscience and Organic Materials (NMMO) Institut de Ciència de Materials de Barcelona (ICMAB-CSIC) and Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Campus Universitari de Bellaterra, Cerdanyola, 08193 Barcelona (Spain)Search for more papers by this authorWe thank the EU through the EC FP7 ONE-P large-scale project (no. 212311), Spain (contracts CTQ2006-06333/BQU and CTQ2010-195011/BQU), the Generalitat de Catalunya (2009SGR00516), the program “Juan de la Cierva” (MICINN), and the CIBER de Bioingeniera, Biomateriales y Nanomedicina (CIBER-BBN), promoted by ISCIII, Spain. We also thank CESGA for the use of their computational resources.
Graphical Abstract
Happy marriage: For the first time, a fused TCNQ–TTF–TCNQ triad has been synthesized and structurally characterized. Strong bending is observed in both the TTF bridge and the benzo-TCNQ moieties, which prevents good packing for intermolecular charge transfer. The Vis/NIR and VT-EPR studies of the mixed-valence derivative of the triad indicate that the electrons are moving from one acceptor moiety to the other through the donor TTF bridge.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
anie_201104841_sm_miscellaneous_information.pdf745.9 KB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1J. F. Wudl, G. M. Smith, E. J. Hufnagel, J. Chem. Soc. D, 1970, 1453; P. Ferraris, D. O. Cowan, V. Walatka, J. H. Perlstein, J. Am. Chem. Soc. 1973, 95, 948; L. B. Coleman, M. J. Cohen, D. J. Sandman, F. G. Yamagishi, A. F. Garito, A. Heeger, Solid State Commun. 1973, 12, 1125.
- 2A. Aviram, M. A. Ratner, Chem. Phys. Lett. 1974, 29, 277.
- 3J. Y. Becker, J. Bernstein, S. Bittner, N. Levi, S. S. Shaik, J. Am. Chem. Soc. 1983, 105, 4468.
- 4 Organic Conductors: Fundamentals and Applications (Ed.: ), Marcel Dekker, New York, 1994.
- 5T. J. Meyer, Acc. Chem. Res. 1989, 22, 163.
- 6J. L. Segura, N. Martín, Angew. Chem. 2001, 113, 1416;
10.1002/1521-3757(20010417)113:8<1416::AID-ANGE1416>3.0.CO;2-N Google ScholarAngew. Chem. Int. Ed. 2001, 40, 1372.10.1002/1521-3773(20010417)40:8<1372::AID-ANIE1372>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
- 7K. Stokbro, J. Taylor, M. Brandbyge, J. Am. Chem. Soc. 2003, 125, 3674.
- 8C. A. Panetta, N. E. Heimer, C. L. Hussey, R. M. Metzger, Synlett 1991, 301.
- 9M. R. Bryce, Adv. Mater. 1999, 11, 11.
- 10F. Dumur, N. Gautier, N. Gallego-Planas, Y. Sahin, E. Levillain, N. Mercier, P. Hudhomme, M. Masino, A. Girlando, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, J. Org. Chem. 2004, 69, 2164; W. H. Watson, E. E. Eduok, R. P. Kashyap, M. Krawiec, Tetrahedron 1993, 49, 3035.
- 11F. Dumur, X. Guégano, N. Gautier, S.-X. Liu, A. Neels, S. Decurtins, P. Hudhomme, Eur. J. Org. Chem. 2009, 6341.
- 12N. Gautier, F. Dumur, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, P. Hudhomme, Angew. Chem. 2003, 115, 2871;
10.1002/ange.200250587 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 2765.
- 13M. R. Bryce, J. Mater. Chem. 2000, 10, 589.
- 14D. F. Perepichka, M. R. Bryce, C. Pearson, M. C. Petty, E. J. L. McInnes, J. P. Zhao, Angew. Chem. 2003, 115, 4784;
10.1002/ange.200351876 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 4635; D. F. Perepichka, M. R. Bryce, Angew. Chem. 2005, 117, 5504;10.1002/ange.200500413 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 5370.
- 15J. Santos, B. M. Illescas, N. Martín, J. Adrio, J. C. Carretero, R. Viruela, E. Ortí, F. Spänig, D. M. Guldi, Chem. Eur. J. 2011, 17, 2957.
- 16E. Tsiperman, J. Y. Becker, V. Khodorkovsky, A. Shames, L. Shapiro, Angew. Chem. 2005, 117, 4083;
10.1002/ange.200500812 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 4015.
- 17A. Aumüller, S. Hünig, Liebigs Ann. Chem. 1984, 618.
- 18A. M. Kini, D. O. Cowan, F. Gerson, R. Möckel, J. Am. Chem. Soc. 1985, 107, 556.
- 19N. Martín, J. L. Segura, C. Seoane, J. Mater. Chem. 1997, 7, 1661.
- 20D. F. Perepichka, M. R. Bryce, A. S. Bastanov, J. A. K. Howard, A. O. Cuello, M. Gray, V. M. Rotello, J. Org. Chem. 2001, 66, 4517.
- 21P. Bando, N. Martin, J. L. Segura, C. Seoane, J. Org. Chem. 1994, 59, 4618.
- 22M. Adam, V. Enkelmann, H. J. Räder, J. Röhrich, K. Müllen, Angew. Chem. 1992, 104, 331; Angew. Chem. Int. Ed. Engl. 1992, 31, 309.
- 23K. Takimiya, K. Imamura, Y. Shibata, Y. Aso, F. Ogura, T. Otsubo, J. Org. Chem. 1997, 62, 5567.
- 24Y. Bando, T. Shirahata, K. Shibata, H. Wada, T. Mori, T. Imakubo, Chem. Mater. 2008, 20, 5119.
- 25N. S. Hush, Prog. Inorg. Chem. 1967, 8, 391.
- 26B. S. Brunschwig, C. Creutz, N. Sutin, Chem. Soc. Rev. 2002, 31, 168.
- 27M. B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 1967, 10, 247.
- 28J. Heinzer, Mol. Phys. 1971, 22, 167; Quantum Chemistry Program Exchange 1972, N° 209. We thank Prof. A. Lund for a copy of this program.
- 29S. F. Rak, L. L. Miller, J. Am. Chem. Soc. 1992, 114, 1388.
- 30T. Mitsuhashi, M. Goto, K. Honda, Y. Maruyama, T. Inabe, T. Sugawara, T. Watanabe, Bull. Chem. Soc. Jpn. 1998, 71, 261.