Double protonation of 1,5-bis(triarylaminoethynyl)anthraquinone to form a paramagnetic pentacyclic dipyrylium salt

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12472-12479

  Rao, Koya Prabhakara ^a   Kusamoto, Tetsuro ^a   Toshimitsu, Fumiyuki ^a   Inayoshi, Kiyotaka ^a   Kume, Shoko ^a   Sakamoto, Ryota ^a   Nishihara, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED MOLECULES; CYCLIZATION REACTIONS; DICATIONS; HOMO-LUMO GAPS; IMIDE-ACID; INTRAMOLECULAR CYCLIZATIONS; MONOPROTONATION; NEUTRAL SPECIES; PARAMAGNETIC BEHAVIOR; PYRYLIUM SALTS; RING COMPOUNDS; TAUTOMERIZATIONS; TRIARYLAMINES;

AROMATIC COMPOUNDS; ELECTROCHEMICAL PROPERTIES; KETONES; MAGNETIC PROPERTIES; ORGANIC POLYMERS; PARAMAGNETIC MATERIALS; PROTONATION;

CYCLIZATION;

1 TRIARYLAMINOETHYNYLANTHRAQUINONE; 1,5 BIS(TRIARYLAMINOETHYNYL)ANTHRAQUINONE; 2,8 BIS(TRIARYLAMINO)BENZO[DE]ISOCHROMENO [1,8 GH]CHROMENE; BIS(TRIFLUOROMETHANESULFONE)IMIDE ACID; CHROMENE DERIVATIVE; QUINONE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; COVALENT BOND; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; MAGNETISM; PROTON TRANSPORT; SYNTHESIS;

ANTHRAQUINONES; CRYSTALLOGRAPHY, X-RAY; MAGNETICS; MODELS, MOLECULAR; PROTONS; PYRANS; SALTS;

EID: 77956232844     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja105250f     Document Type: Article

References (52)

1. Joachim, C., Gimzewski, J. K., and Aviram, A. Nature. 2000, 408, 541-548
2. Seminario, J. M. Nat. Mater. 2005, 4, 111-113
3. Ehli, C., Oelsner, C., Guldi, D. M., Mateo-Alonso, A., Prato, M., Schmidt, C., Backes, C., Hauke, F., and Hirsch, A. Nat. Chem. 2009, 1, 243-249
4. Sato, O., Tao, J., and Zhang, Y.-Z. Angew. Chem., Int. Ed. 2007, 46, 2152-2187
5. Mativetsky, J. M., Pace, G., Elbing, M., Rampi, M. A., Mayor, M., and Samorià, P. J. Am. Chem. Soc. 2008, 130, 9192-9193
6. Klajn, R., Fang, L., Coskun, A., Olson, M. A., Wesson, P. J., Stoddart, J. F., and Grzybowski, B. A. J. Am. Chem. Soc. 2009, 131, 4233-4235
7. Champin, B., Mobian, P., and Sauvage, J.-P. Chem. Soc. Rev. 2007, 36, 358-366
8. Kume, S., Murata, M., Ozeki, T., and Nishihara, H. J. Am. Chem. Soc. 2005, 127, 490-491
9. Sakamoto, R., Murata, M., Kume, S., Sampei, S., Sugimoto, M., and Nishihara, H. Chem. Commun. 2005, 1215-1217
10. Muratsugu, S., Kume, S., and Nishihara, H. J. Am. Chem. Soc. 2008, 130, 7204-7205
11. Sakamoto, A., Hirooka, A., Namiki, K., Kurihara, M., Murata, M., Sugimoto, M., and Nishihara, H. Inorg. Chem. 2005, 44, 7547-7558
12. Colbran, S. B., Lee, S. T., Lonnon, D. G., Maharaj, F. J. D., McDonagh, A. M., Walker, K. A., and Young, R. D. Organometallics 2006, 25, 2216-2224
13. Kondo, M., Murata, M., Nishihara, H., Nishibori, E., Aoyagi, S., Yoshida, M., Kinoshita, Y., and Sakata, M. Angew. Chem., Int. Ed. 2006, 45, 5461-5464
14. Ratera, I., Molina, D. R., Renz, F., Ensling, J., Wurst, K., Rovira, C., Gütlich, P., and Veciana, J. J. Am. Chem. Soc. 2003, 125, 1463-1464
15. Jiao, J., Long, G. J., Grandjean, F., Beatty, A. M., and Fehlner, T. P. J. Am. Chem. Soc. 2003, 125, 7522-7523
16. Nishihara, H. Adv. Inorg. Chem. 2002, 53, 41-86
17. Hillard, E., Vessieres, A., Thouin, L., Jaouen, G., and Amatore, C. Angew. Chem., Int. Ed. 2006, 45, 285-290
18. Albinati, A., Fabrizi de Biani, F., Leoni, P., Marchetti, L., Pasquali, M., Rizzato, S., and Zanello, P. Angew. Chem., Int. Ed. 2005, 44, 5701-5705
19. Green, J. E., Choi, J. W., Boukai, A., Bunimovich, Y., Halperin, E. J., DeIonno, E., Luo, Y., Sheriff, B. A., Xu, K., Shin, Y. S., Tseng, H.-R., Stoddart, J. F., and Heath, J. R. Nature 2007, 445, 414-417
20. Irie, M. Chem. Rev. 2000, 100, 1685-1716
21. Sakamoto, R., Kume, S., and Nishihara, H. Chem.-Eur. J. 2008, 14, 6978-6986
22. Nagashima, S., Murata, M., and Nishihara, H. Angew. Chem., Int. Ed. 2006, 45, 4298-4301
23. Gabelica, V. and Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841
24. Rowan, S. J., Cantrill, S. J., Cousins, G. R. L., Sanders, J. K. M., and Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952
25. Arai, R., Uemura, S., Irie, M., and Matsuda, K. J. Am. Chem. Soc. 2008, 130, 9371-9379
26. Duriska, M. B., Neville, S. M., Moubaraki, B., Cashion, J. D., Halder, G. J., Chapman, K. W., Balde, C., Lětard, J.-F., Murray, K. S., Kepert, C. J., and Batten, S. R. Angew. Chem., Int. Ed. 2009, 48, 2549-2552
27. Dediu, V. A., Hueso, L. E., Bergenti, I., and Taliani, C. Nat. Mater. 2009, 8, 707-716
28. Gundlach, D. J. Nat. Mater. 2008, 7, 216-221
29. Huang, Y. S., Westenhoff, S., Avilov, I., Sreearunothai, P., Hodgkiss, J. M., Deleener, C., Friend, R. H., and Beljonne, D. Nat. Mater. 2008, 7, 483-489
30. Tian, H., Yang, X., Pan, J., Chen, R., Liu, M., Zhang, Q., Hagfeldt, A., and Sun, L. Adv. Funct. Mater. 2008, 18, 3461-3468
31. Ross, R. B., Cardona, C. M., Guldi, D. M., Sankaranarayanan, S. G., Reese, M. O., Kopidakis, N., Peet, J., Walker, B., Bazan, G. C., Van Keuren, E., Holloway, B. C., and Drees, M. Nat. Mater. 2009, 8, 208-212
32. Qian, G., Zhong, Z., Luo, M., Yu, D., Zhang, Z., Wang, Z. Y., and Ma, D. Adv. Mater. 2009, 21, 111-116
33. Park, S., Seo, J., Kim, S. H., and Park, S. Y. Adv. Funct. Mater 2008, 18, 726-731
34. Murata, M., Fujita, T., Yamada, M., Kurihara, M., and Nishihara, H. Chem. Lett. 2000, 1328-1329
35. Kondo, M., Uchikawa, M., Zhang, W.-W., Namiki, K., Kume, S., Murata, M., Kobayashi, Y., and Nishihara, H. Angew. Chem., Int. Ed. 2007, 46, 6271-6274
36. Kondo, M., Uchikawa, M., Namiki, K., Zhang, W., Kume, S., Nishibori, E., Suwa, H., Aoyagi, S., Sakata, M., Murata, M., Kobayashi, Y., and Nishihara, H. J. Am. Chem. Soc. 2009, 131, 12112-12124
37. Tao, J., Maruyama, H., and Sato, O. J. Am. Chem. Soc. 2006, 128, 1790-1791
38. Diallo, A. K., Daran, J.-C., Varret, F., Ruiz, J., and Astruc, D. Angew. Chem., Int. Ed. 2009, 48, 3141-3145
39. Mochida, T., Takazawa, K., Matsui, H., Takahashi, M., Takeda, M., Sato, M., Nishio, Y., Kajita, K., and Mori, H. Inorg. Chem. 2005, 44, 8628-8641
40. Salamon, S. B., Brewer, S. H., Depperman, E. C., Franzen, S., Kampf, J. W., Kirk, M. L., Kumar, R. K., Lappi, S., Peariso, K., Preuss, K. E., and Shultz, D. A. Inorg. Chem. 2006, 45, 4461-4467
41. Hearns, N. G. R., Koreàok, J. L., Paquette, M. M., and Preuss, K. E. Inorg. Chem. 2006, 45, 8817-8819
42. Rotthaus, O., Thomas, F., Jarjayes, O., Philouze, C., Saint-Aman, E., and Pierre, J.-L. Chem.-Eur. J. 2006, 12, 6953-6962
43. Naumov, P. and Belik, A. A. Inorg. Chem. Commun. 2008, 11, 465-469
44. Kiriya, D., Chang, H.-C., Nakamura, K., Tanaka, D., Yoneda, K., and Kitagawa, S. Chem. Mater. 2009, 21, 1980-1988
45. Kondo, M., Uchikawa, M., Kume, S., and Nishihara, H. Chem. Commun. 2009, 15, 1993-1995
46. Murata, M., Yamada, M., Fujita, T., Kojima, K., Kurihara, M., Kubo, K., Kobayashi, Y., and Nishihara, H. J. Am. Chem. Soc. 2001, 123, 12903-12904
47. Hirao, Y., Urabe, M., Ito, A., and Tanaka, K. Angew. Chem., Int. Ed. 2007, 46, 3300-3303
48. Sandberg, M. O., Nagao, O., Wu, Z., Matsushita, M. M., and Sugawara, T. Chem. Commun. 2008, 3738-3740
49. Lambert, C., Nöll, G., Schmälzlin, E., Meerholz, K., and Bräuchele, C. Chem.-Eur. J. 1998, 4, 2129-2135
50. Sheldrick, G. M. Program for Crystal Structure Solution; University of Göttingen: Germany, 1997.
51. Sheldrick, G. M. Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
52. Frisch, M. J.; et al. Gaussian 03, revision-B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.