Synthesis and properties of dithienometallole-pyridinochalcogenadiazole alternate polymers

Polymer Journal

Volumn 45, Issue 9, 2013, Pages 979-984

  Ohshita, Joji ^a   Miyazaki, Masayuki ^a   Zhang, Fei Bao ^a   Tanaka, Daiki ^a   Morihara, Yasushi ^b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b KURARAY CO LTD   (Japan)

Author keywords

Bulk heterojunction; Dithienometallole; Donor acceptor interaction; p conjugated polymer; Polymer solar cell

Indexed keywords

BULK HETEROJUNCTION; CHLOROBENZENE SOLUTION; DITHIENOMETALLOLE; DONOR-ACCEPTOR INTERACTION; MAXIMUM POWER; POLYMER SOLAR CELLS; STILLE COUPLING REACTION; ULTRAVIOLET-VISIBLE ABSORPTION SPECTRUM;

GERMANIUM; HETEROJUNCTIONS; SOLAR CELLS;

POLYMER FILMS;

EID: 84876908383     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2013.13     Document Type: Article

References (24)

1. Ohshita, J., Kai, H., Takata, A., Iida, T., Kunai, A., Ohta, N., Komaguchi, K., Shiotani, M., Adachi, A., Sakamaki, K. & Okita, K. Effects of conjugated substituents on the optical, electrochemical, and electron-transporting properties of dithienosiloles. Organometallics 20, 4800 (2001).
2. Kim, D.-H., Ohshita, J., Lee, K.-H., Kunugi, Y. & Kunai, A. Synthesis of p-conjugated oligomers containing dithienosilole units. Organometallics 25, 1511 (2006).
3. Zeng, W., Cao, Y., Bai, Y., Wang, Y., Shi, Y., Zhang, M., Wang, F., Pan, C. & Wang, C. Efficient dye-sensitized solar cells with an organic photosensitizer featuring orderly conjugated ethylenedioxythiophene and dithienosilole blocks. Chem. Mater. 22, 1915 (2010).
4. Chen, J. & Cao, Y. Silole-containing polymers: chemistry and optoelectronic properties. Macromol. Rapid Commun. 28, 1714 (2007).
5. Ohshita, J. Conjugated oligomers and polymers containing dithienosilole units. Macrmol. Chem. Phys. 210, 1360 (2009).
6. Ohshita, J., Nodono, M., Watanabe, T., Kunai, A., Harima, Y., Yamashita, K. & Ishikawa, M. Synthesis and properties of dithienosiloles. J. Organomet. Chem. 553, 487 (1998).
7. Ohshita, J., Nodono, M., Kai, H., Watanabe, T., Kunai, A., Komaguchi, K., Shiotani, A., Okita, K., Harima, Y., Yamashita, K. & Ishikawa, M. Synthesis and optical, electrochemical, and electron-transporting properties of silicon-bridged bithiophenes. Organometallics 18, 1453 (1999).
8. Hou, J., Chen, H.-Y., Zhang, S., Li, G. & Yang, Y. Synthesis, characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole. J. Am. Chem. Soc. 130, 16144 (2008).
9. Huo, L., Chen, H.-Y., Hou, J., Chen, T. L. & Yang, Y. Low band gap dithieno [3,2-b:2',3'-d]silole-containing polymers, synthesis, characterization and photovoltaic application. Chem. Commun. 37, 5570 (2009).
10. Min, J., Zhang, Z.-G., Zhang, S., Zhang, M., Zhang, J. & Li, Y. Synthesis and photovoltaic properties of DA copolymers based on dithienosilole and benzotriazole. Macromolecules 44, 7632 (2011).
11. Zhang, M., Guo, X., Zhang, Z.-G. & Li, Y. D-A copolymers based on dithienosilole and phthalimide for photovoltaic materials. Polymer 52, 5464 (2011).
12. Peet, J., Wen, L., Byrne, P., Rodman, S., Forberich, K., Shao, Y., Drolet, N. & Gaudiana, R. Bulk heterojunction solar cells with thick active layers and high fill factors enabled by a bithiophene-co-thiazolothiazole push-pull copolymer. Appl. Phys. Lett. 98, 043301 (2011).
13. Subramaniyan, S., Xin, H., Kim, F. S., Shoaee, S., Durrant, J. R. & Jenekhe, S. A. Effects of side chains on thiazolothiazole-based copolymer semiconductors for high performance solar cells.. Adv. Energy Mater. 1, 854 (2011).
14. Subramaniyan, S., Xin, H., Kim, F. S. & Jenekhe, S. A. New thiazolothiazole copolymer semiconductors for highly efficient solar cells. Macromolecules 44, 6245 (2011).
15. Chu, T.-Y., Lu, J., Beaupre, S., Zhang, Y., Pouliot, J.-R., Wakim, S., Zhou, J., Leclerc, M., Li, Z., Ding, J. & Tao, Y. Bulk heterojunction solar cells using thieno[3,4-c]pyrrole- 4,6-dione and dithieno[3,2-b:20,30-d]silole copolymer with a power conversion efficiency of 7.3%. J. Am. Chem. Soc. 133, 4250 (2011).
16. Ohshita, J., Hwang, Y.-M., Mizumo, T., Yoshida, H., Ooyama, Y., Hariam, Y. & Kunugi, Y. Synthesis of dithienogermole-containing p-conjugated polymers and applications to photovoltaic cells. Organometallics 30, 3233 (2011).
17. Amb, C. M., Graham, K. R., Subbiah, J., Small, C. E., So, F. & Reynolds, J. R. Dithienogermole as a fused electron donor in bulk heterojunction solar cells. J. Am. Chem. Soc. 133, 10062 (2011).
18. Gendron, D., Morin, P.-O., Berrouard, P., Allard, N., Aïch, B. R., Garon, C. N., Tao, Y. & Leclerc, M. Synthesis and photovoltaic properties of Poly(dithieno[3,2-b: 20,30-d]- germole) derivatives. Macromolecules 44, 7188 (2011).
19. Hwang, Y.-M., Ohshita, J., Harima, Y., Mizumo, T., Ooyama, Y., Morihara, Y., Izawa, T., Sugioka, T. & Fujita, A. Synthesis, characterization, and photovoltaic applications of dithienogermole-dithienylbenzothiadiazole and -dithienylthiazolothiazole copolymers. Polymer 52, 3912 (2011).
20. Henson, Z. B., Welch, G. C., van der Poll, T. & Bazan, G. C. Pyridalthiadiazole-based narrow band gap chromophores. J. Am. Chem. Soc. 134, 3766 (2012).
21. Miller, S. A., Stuart, A. C., Womick, J. M., Zhou, H., You, W. & Moran, A. M. Excitedstate photophysics in a low band gap polymer with high photovoltaic efficiency. J. Phys. Chem. C. 115, 2371 (2011).
22. Sun, Y., Chien, S.-C., Yip, H.-L., Zhang, Y., Chen, K.-S., Zeigler, D. F., Chen, F.-C., Lin, B. & Jen, K.-Y. High-mobility low-bandgap conjugated copolymers based on indacenodithiophene and thiadiazolo[3,4-c]pyridine units for thin film transistor and photovoltaic applications. J. Mater. Chem. 21, 13247 (2011).
23. Lee, J. K., Ma, W. L., Brabec, C. J., Yuen, J., Moon, J. S., Kim, J. Y., Lee, K., Bazan, G. C. & Heeger, A. J. Processing additives for improved efficiency from bulk heterjunction solar cells. J. Am. Chem. Soc. 130, 3619 (2008).
24. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P. A., Izmaylov, F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, Jr. J. A., Peralta, J., Ogliaro, E. F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., 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., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. Gaussian 09 Revision A.02 (Gaussian Inc, Wallingford, CT, USA, 2009).