Star-shaped tetrathiafulvalene-fused coronene with large π-extended conjugation

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5727-5729

  Jia, Hong Peng ^a   Liu, Shi Xia ^a   Sanguinet, Lionel ^b   Levillain, Eric ^b   Decurtins, Silvio ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b UNIVERSITÉ D'ANGERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NEAR INFRARED SPECTROSCOPY;

CORONENE; EXTENDED CONJUGATION; MULTI-ELECTRON; OPTICAL SPECTRA; STAR-SHAPED; TETRATHIAFULVALENES; TRI STARS; UV-VIS-NIR SPECTROSCOPY;

ELECTRONIC PROPERTIES;

CORONENE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CROSS COUPLING REACTION; ELECTROCHEMISTRY; NEAR INFRARED SPECTROSCOPY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 68049104237     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901054b     Document Type: Article

References (28)

1. (a) Mynar, J. L.; Yamamoto, T.; Kosaka, A.; Fukushima, T.; Ishii, N.; Aida, T. J. Am. Chem. Soc. 2008, 130, 1530.
2. (b) Yamamoto, T.; Fukushima, T.; Kosaka, A.; Jin, W.; Yamamoto, Y.; Ishii, N.; Aida, T. Angew. Chem., Int. Ed. 2008, 47, 1672.
3. (c) Carbon-Rich Compounds; Haley, M. M., Tykwinski, R. R., Eds.; Wiley-VCH, Verlag GmbH and Co., KGaA: Weinheim, Germany, 2006.
4. (d) Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452.
5. (e) Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Science 2004, 304, 1481.
6. (a) van de Craats, A. M.; Warman, J. M.; Fechtenkötter, A.; Brand, J. D.; Harbison, M. A.; Müllen, K. Adv. Mater. 1999, 11, 1469.
7. (b) Palermo, V.; Morelli, S.; Simpson, C.; Müllen, K.; Samori, P. J. Mater. Chem. 2006, 16, 266.
8. (c) Xiao, S.; Tang, J.; Beetz, T.; Guo, X.; Tremblay, N.; Siegrist, T.; Zhu, Y.; Steigerwald, M.; Nuckolls, C. J. Am. Chem. Soc. 2006, 128, 10700.
9. (a) Alibert-Fouet, S.; Seguy, I.; Bobo, J.-F.; Destruel, P.; Bock, H. Chem. - Eur. J. 2007, 13, 1746.
10. (b) Shen, H. C.; Tang, J. M.; Chang, H. K.; Yang, C. W.; Liu, R. S. J. Org. Chem. 2005, 70, 10113.
11. (c) Rieger, R.; Kastler, M.; Enkelmann, V.; Müllen, K. Chem. - Eur. J. 2008, 14, 6322.
12. (a) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372.
13. (b) Yamada, J.; Sugimoto, T. TTF Chemistry. Fundamentals and applications of Tetrathiafulvalene; Springer: Berlin, Germany, 2004.
14. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
15. (b) Díaz, M. C.; Illescas, B. M.; Martín, N.; Perepichka, I. F.; Bryce, M. R.; Levillain, E.; Viruela, R.; Ortí, E. Chem. - Eur. J. 2006, 12, 2709.
16. (c) Wu, J.-C.; Liu, S.-X.; Neels, A.; Le Derf, F.; Sallé, M.; Decurtins, S. Tetrahedron 2007, 63, 11282.
17. (d) Goze, C.; Leiggener, C.; Liu, S.-X.; Sanguinet, L.; Levillain, E.; Hauser, A.; Decurtins, S. ChemPhysChem 2007, 8, 1504.
18. (e) Guldi, D. M.; Giacalone, F.; de la Torre, G.; Segura, J. L.; Martin, N. Chem. - Eur. J. 2005, 11, 7199.
19. (f) Giacalone, F.; Segura, J. L.; Martín, N.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 5340.
20. (g) Wielopolski, M.; Atienza, C.; Clark, T.; Guldi, D. M.; Martín, N. Chem. - Eur. J. 2008, 14, 6379.
21. (a) Gautier, N.; Dumur, F.; Lloveras, V.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C.; Hudhomme, P. Angew. Chem., Int. Ed. 2003, 42, 2765.
22. (b) Guégano, X.; Kanibolotsky, A. L.; Blum, C.; Mertens, S. F. L.; Liu, S.-X.; Neels, A.; Hagemann, A. H.; Skabara, P. J.; Leutwyler, S.; Wandlowski, T.; Hauser, A.; Decurtins, S. Chem. - Eur. J. 2009, 15, 63.
23. (c) Jia, C.-Y.; Liu, S.-X.; Tanner, C.; Leiggener, C.; Sanguinet, L.; Levillain, E.; Leutwyler, S.; Hauser, A.; Decurtins, S. Chem. Commun. 2006, 1878.
24. (d) Loosli, C.; Jia, C.-Y.; Liu, S.-X.; Haas, M.; Dias, M.; Levillain, E.; Neels, A.; Labat, G.; Hauser, A.; Decurtins, S. J. Org. Chem. 2005, 70, 4988.
25. (e) Jia, C.-Y.; Liu, S.-X.; Tanner, C.; Leiggener, C.; Neels, A.; Sanguinet, L.; Levillain, E.; Leutwyler, S.; Hauser, A.; Decurtins, S. Chem. - Eur. J. 2007, 13, 3804.
26. Tanner, D.; Wennerström, O.; Norinder, U. Tetrahredron 1986, 42, 4499.
27. Gingras, M.; Pinchart, A.; Dallaire, C.; Mallah, T.; Levillain, E. Chem. - Eur. J. 2004, 10, 2895.
28. 3+) by changing the solvent conditions were not successful.