Electron- or hole-transporting nature selected by side-chain-directed π-stacking geometry: Liquid crystalline fused metalloporphyrin dimers

Journal of the American Chemical Society

Volumn 133, Issue 17, 2011, Pages 6537-6540

  Sakurai, Tsuneaki ^a   Tashiro, Kentaro ^b   Honsho, Yoshihito ^c   Saeki, Akinori ^c   Seki, Shu ^c   Osuka, Atsuhiro ^d   Muranaka, Atsuya ^e   Uchiyama, Masanobu ^a,e   Kim, Jungeun ^f   Ha, Sunyeo ^a   Kato, Kenichi ^g   Takata, Masaki ^a,f,g   Aida, Takuzo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^c OSAKA UNIVERSITY   (Japan)

^d KYOTO UNIVERSITY   (Japan)

^e INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^f JAPAN SYNCHROTRON RADIATION RESEARCH INSTITUTE   (Japan)

^g RIKEN Harima Institute Research   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEXES; ELECTROACTIVE CORE; HOLE TRANSPORTING; LIQUID-CRYSTALLINE; MESOPHASES; METALLOPORPHYRINS; N-TYPE SEMICONDUCTORS; P TYPE SEMICONDUCTOR; PORPHYRIN DIMERS; SIDE CHAINS; SIDE-CHAIN; TIME OF FLIGHT; TRANSIENT PHOTOCURRENTS;

COPPER COMPOUNDS; CRYSTALLINE MATERIALS; ELECTRONIC PROPERTIES; LIQUIDS;

PORPHYRINS;

COPPER COMPLEX; METALLOPORPHYRIN;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; ELECTRON TRANSPORT; GEOMETRY; LIQUID CRYSTAL; SEMICONDUCTOR; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION;

COPPER; DIMERIZATION; ELECTRONS; LIQUID CRYSTALS; METALLOPORPHYRINS; SEMICONDUCTORS;

EID: 79955432525     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201272t     Document Type: Article

References (35)

1. Pron, A.; Gawrys, P.; Zagorska, M.; Djurado, D.; Demadrille, R. Chem. Soc. Rev. 2010, 39, 2577-2632
2. Brédas, J.-L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971-5003
3. Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359-369
4. Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296-1323
5. Wu, W.; Liu, Y.; Zhu, D. Chem. Soc. Rev. 2010, 39, 1489-1502
6. Tsuda, A.; Furuta, H.; Osuka, A. Angew. Chem. Int. Ed. 2000, 39, 2549-2552
7. Tsuda, A.; Osuka, A. Science 2001, 293, 79-82
8. Ikeda, T.; Aratani, N.; Osuka, A. Chem. Asian J. 2009, 4, 1248-1256
9. Sakurai, T.; Shi, K.; Sato, H.; Tashiro, K.; Osuka, A.; Saeki, A.; Seki, S.; Tagawa, S.; Sasaki, S.; Masunaga, H.; Osaka, K.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2008, 130, 13812-13813
10. Hains, A. W.; Liang, Z.; Woodhouse, M. A.; Gregg, B. A. Chem. Rev. 2010, 110, 6689-6735
11. Zimmerman, J. D.; Diev, V. V.; Hanson, K.; Lunt, R. R.; Yu, E. K.; Thompson, M. E.; Forrest., S. R. Adv. Mater. 2010, 22, 2780-2783
12. See Supporting Information.
13. Percec, V.; Johansson., G.; Ungar, G.; Zhou, J. J. Am. Chem. Soc. 1996, 118, 9855-9866
14. Percec, V.; Glodde, M.; Peterca, M.; Rapp, A.; Schnell, I.; Spiess, H. W.; Bera, T. K.; Miura, Y.; Balagurusamy, V. S. K.; Aqad, E.; Heiney, P. H. Chem. Eur. J. 2006, 12, 6298-6314
15. Tschierske, C. Chem. Soc. Rev. 2007, 36, 1930-1970
16. Lehmann, M. Chem. Eur. J. 2009, 15, 3638-3651
17. Lehmann, M.; Jahr, M.; Gutmann, J. J. Mater. Chem. 2008, 14, 2995-3003
18. Yang, W. -Y.; Ahn, J. -H.; Yoo, Y. -S.; Oh, N. -K.; Lee, M. Nat. Mater. 2005, 4, 399-402
19. Lehmann, M.; Jahr, M.; Donnio, B.; Graf, R.; Gemming, S.; Popov, I. Chem. Eur. J. 2008, 14, 3562-3576
20. Maiti, N. C.; Mazumdar, S.; Periasamy, N. J. Phys. Chem. B 1998, 102, 1528-1538
21. Helmich, F.; Lee, C. C.; Nieuwenhuizen, M. M. L.; Gielen, J. C.; Christianen, P. C. M.; Larsen, A.; Fytas, G.; Leclère, P. E. L. G.; Schenning, A. P. H. J.; Meijer, E. W. Angew. Chem. Int. Ed. 2010, 49, 3939-3942
22. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534
23. Shearman, G. C.; Yahioglu, G.; Kirstein, J.; Milgrom, L. R.; Seddon, J. M. J. Mater. Chem. 2009, 19, 598-604
24. Ohta, K.; Yamaguchi, N.; Yamamoto, I. J. Mater. Chem. 1998, 8, 2637-2650
25. hetero, the hole mobility estimated was several times smaller than the electron mobility.
26. Saeki, A.; Seki, S.; Sunagawa, T.; Ushida, K.; Tagawa, S. Philos. Mag. 2006, 86, 1261-1276
27. Saeki, A.; Seki, S.; Takenobu, T.; Iwasa, Y.; Tagawa, S. Adv. Mater. 2008, 20, 920-923
28. Cornil, J.; Lemaur, V.; Calbert, J. P.; Brédas, J.-L. Adv. Mater. 2002, 14, 726-729
29. Lemaur, V.; Da Silva Filho, D. A.; Coropceanu, V.; Lehmann, M.; Geerts, Y.; Piris, J.; Debije, M.; Van de Craats, A.; Senthilkumar, K.; Siebbeles, L.; Warman, J.; Brédas, J.-L.; Cornil, J. J. Am. Chem. Soc. 2004, 126, 3271-3279
30. Marcon, V.; Breib., D. W.; Pisula, W.; Dahl, J.; Kirkpatrick, J.; Patwardhan, S.; Grozema, F.; Andrienko, D. J. Am. Chem. Soc. 2009, 131, 11426-11432
31. Cornil, J.; Brédas, J.-L.; Zaumseil, J.; Sirringhauso, H. Adv. Mater. 2007, 19, 1791-1799
32. Feng, X.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Nat. Mater. 2009, 8, 421-426
33. Li, W.-S.; Yamamoto, Y.; Fukushima, T.; Saeki, A.; Seki, S.; Tagawa, S.; Masunaga, H.; Sasaki, S.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2008, 130, 8886-8887
34. Iino, H.; Hanna, J.; Bushby, R. J.; Movaghar, B.; Whitaker, B. J.; Cook, M. Appl. Phys. Lett. 2005, 87, 132102
35. Kato, K.; Hirose, R.; Takemoto, M.; Ha, S.; Kim, J.; Higuchi, M.; Matsuda, R.; Kitagawa, S.; Takata, M. AIP Conf. Proc. 2010, 1234, 875-878