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Synthesis, Photophysical and Electrochemical Properties of Novel Conjugated Donor-Acceptor Molecules Based on Phenothiazine and Benzimidazole
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 Title & Authors
Synthesis, Photophysical and Electrochemical Properties of Novel Conjugated Donor-Acceptor Molecules Based on Phenothiazine and Benzimidazole
Zhang, Xiao-Hang; Kim, Seon-Ho; Lee, In-Su; Gao, Chun-Ji; Yang, Sung-Ik; Ahn, Kwang-Hyun;
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Two series of new organic fluorophores such as asymmetrical 3-(benzimidazol-2-yl)-10-hexylphenothiazine derivatives 1 and symmetrical 3,7-bis(benzimidazol-2-yl)-10-hexylphenothiazine derivatives 2 have been synthesized. Electronic absorption, fluorescence, and electrochemistry measurements reveal that the electron withdrawing benzimidazole subunit directly connected to the phenothiazine core facilitates the charge transfer characters which were also verified by the theoretical calculations. Various substituents on the benzimidazole moieties can allow a fine-tuning of the LUMO energy levels of the molecules without significantly affecting the HOMO energy levels. The method provides a new route for designing ambipolar molecules whose energy levels are well-matched with the Fermi levels of the electrodes to facilitate the electron or hole injection/transfer in OLED devices.
Phenothiazine;Benzimidazole;Charge transfer;Donor-acceptor;Fluorophore;
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Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610-3616 crossref(new window)

Chen, C. H.; Shi, J.; Tang, C. W.; Klubek, K. P. Thin Solid Film 2000, 363, 327-331 crossref(new window)

Tao, X. T.; Miyata, S.; Sasabe, H.; Zhang, G. J.; Wada, T.; Jiang, M. H. Appl. Phys. Lett. 2001, 78, 279-281 crossref(new window)

Thomas, K. R. J.; Lin, J. T.; Tao, Y.-T.; Chuen, C.-H. Chem. Mater. 2002, 14, 2796-2802 crossref(new window)

Thomas, K. R. J.; Lin, J. T.; Tao, Y.-T.; Chuen, C.-H. Adv. Mater. 2002, 14, 822-826 crossref(new window)

Chen, C.-T.; Lin, J.-S.; Moturu, M. V. R. K.; Lin, Y.-W.; Yi, W.; Tao, Y.-T.; Chien, C.-H. Chem. Commun. 2005, 3980-3982

Chen, S.; Xu, X.; Liu, Y.; Yu, G.; Sun, X.; Qiu, W; Ma, Y.; Zhu, D. Adv. Funct. Mater. 2005, 15, 1541-1546 crossref(new window)

Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874 crossref(new window)

Abbotto, A.; Beverina, L.; Bozio, R.; Facchetti, A.; Ferrante, C.; Pagani, G. A.; Pedron, D.; Signorini, R. Chem. Commun. 2003, 2144-2145

Lai, R. Y.; Fabrizio, E. F.; Lu, L.; Jenekhe, S. A.; Bard, A. J. J. Am. Chem. Soc. 2001, 123, 9112-9118 crossref(new window)

Cho, M. J.; Kim, J. Y.; Kim, J. H.; Lee, S. H.; Dalton, L. R.; Choi, D. H. Bull. Korean Chem. Soc. 2005, 26, 77-84 crossref(new window)

Wong, M. S.; Li, Z. H.; Tao, Y.; D'orio, M. Chem. Mater. 2003, 15, 1198-1203 crossref(new window)

Jiao, G. S.; Thoreson, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668-14669 crossref(new window)

Kannan, R.; He, G. S.; Yuan, L.; Xu, F.; Prasad, P.; Dombroskie, A. G. Chem. Mater. 2001, 13, 1896-1904 crossref(new window)

Chiang, C.-L.; Shu, C.-F.; Chen, C.-T. Org. Lett. 2005, 7, 3717-3720 crossref(new window)

Thomas, K. R. J.; Lin, J. T.; Velusamy, M.; Tao, Y.-T.; Chuen, C.-H. Adv. Funct. Mater. 2004, 14, 83-90 crossref(new window)

Li, Z. H.; Wong, M. S.; Fukutami, H.; Tao, Y. Chem. Mater. 2005, 17, 5032-5040 crossref(new window)

Yasuda, T.; Imase, T.; Yamamoto, T. Macromolecules 2005, 38, 7378-7385 crossref(new window)

Ko, C.-W.; Tao, Y. T.; Danel, A.; Krzeminska, L.; Tomasik, P. Chem. Mater. 2001, 13, 2441-2446 crossref(new window)

Krebs, F. C.; Spanggaard, H. J. Org. Chem. 2002, 67, 7185-7192 crossref(new window)

Liang, F.; Zhou, Q.; Cheng, Y.; Wang, L.; Ma, D.; Jing, X.; Wang, F. Chem. Mater. 2003, 15, 1935-1937 crossref(new window)

Huang, W.-S.; Lin, J.; Chien, C.-H.; Tao, Y.-T.; Sun, S.-S.; Wen, Y.-S. Chem. Mater. 2004, 16, 2480-2488 crossref(new window)

Wang, R.-Y.; Jia, W.-L.; Aziz, H.; Vamvounis, G.; Wang, S.; Hu, N.-X.; Popovic, Z. D.; Coggan, J. A. Adv. Funct. Mater. 2005, 15, 1483-1487 crossref(new window)

Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556-4573 and references therein crossref(new window)

Spreitzer, H.; Daub, J. Chem. Eur. J. 1996, 2, 1150-1158 crossref(new window)

Kramer, C. S.; Muller, T. J. J. Eur. J. Org. Chem. 2003, 3534-3548

Sailer, M.; Nonnenmacher, M.; Oeser, T.; Muller, T. J. J. Eur. J. Org. Chem. 2006, 423-435

Lai, R. Y.; Kong, X.; Jenekhe, S. A.; Bard, A. J. J. Am. Chem. Soc. 2003, 125, 12631-12639 crossref(new window)

Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 36, 7315-7324

Kong, X.; Kulkarni, A. P.; Jenekhe, S. A. Macromolecules 2003, 36, 8992-8999 crossref(new window)

Hwang, D.; Kim, S.; Park, M.; Lee, J.; Koo, B.; Kang, I.; Kim, S.; Zyung, T. Chem. Mater. 2004, 16, 1298-1303 crossref(new window)

Sun, X.; Liu, Y.; Xu, X.; Yang, C.; Yu, G.; Chem, S.; Zhao, Z.; Qiu, W.; Li, Y.; Zhu, D. J. Phys. Chem. B 2005, 109, 10786-10792 crossref(new window)

Weiss, E. A.; Tauber, M. J.; Kelley, R. F.; Ahrens, M. J.; Ratner, M. A.;Wasielewski, M. R. J. Am. Chem. Soc. 2005, 127, 11842-11850 crossref(new window)

Zhang, X.-H.; Choi, S.-H.; Choi, D. H.; Ahn, K.-H. Tetrahedron Lett. 2005, 46, 5273-5376. crossref(new window)

Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578-5587 crossref(new window)

Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004

Li, X. C.; Liu, Y. Q.; Liu, M. S.; Jen, A. K. Y. Chem. Mater. 1999, 11, 1568-1575 crossref(new window)

Otwinowsky, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology Carter, C. W., Sweet, R. M., Eds.; Academic Press: New York, 1996; Vol. 276, pp 307-326

Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures University of Gottingen: Gottingen, Germany, 1997