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Suzuki cross-coupling reactions of 4,7-dibromo[1, 2, 5]selenadiazolo[3,4-c]pyridine – a path to new solar cell components

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Chemistry of Heterocyclic Compounds Aims and scope

A study of Suzuki cross-coupling reactions of 4,7-dibromo[1, 2, 5]selenadiazolo[3,4-c]pyridine resulted in the first synthesis of photosensitizers on the basis of [1, 2, 5]selenadiazolo[3,4-c]pyridine system. Optical and electrochemical properties of the obtained dyes were studied and were found to meet the requirements for photosensitizers that can be used for the creation of organic solar cells.

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References

  1. Zhao, J.; Wang, A.; Green. M. A. Sol. Energy Mater. Sol. Cells 2001, 65, 429.

  2. Graetzel, M.; Janssen, R. A. J.; Mitzi, D. B.; Sargent, E. H. Nature 2012, 488, 304.

    Article  CAS  Google Scholar 

  3. Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Chem. Rev. 2010, 110, 6595.

    Article  CAS  Google Scholar 

  4. Neto, B. A. D.; Lapis, A. A. M.; da Silva Júnior, E. N.; Dupont, J. Eur. J. Org. Chem. 2013, 228.

  5. Knyazeva, E. A.; Rakitin, O. A. Russ. Chem. Rev. 2016, 85, 1146. [Usp. Khim. 2016, 85, 1146.]

  6. Wang, D.; Zhang, X.; Ding, W.; Zhao, X.; Geng, Z. Comput. Theor. Chem. 2014, 1029, 68.

    Article  CAS  Google Scholar 

  7. Bolshakov, O. I.; Grishina, M. A.; Galushko, A.; Potemkin, V. A.; Rakitin, O. A. J. Chem. 2015, ID 467593, http://dx.doi.org/10.1155/2015/467593.

  8. Ohshita, J.; Miyazaki, M.; Zhang, F.-B.; Tanaka, D.; Morihara, Y. Polym. J. 2013, 45, 979.

    Article  CAS  Google Scholar 

  9. Oshita, J.; Harima, Y.; Morihara, Y.; Fujita, A.; Shibuya, H.; Fukumoto, T. Jpn. Patent 2013237813.

  10. Konstantinova, L. S.; Knyazeva, E. A.; Rakitin, O. A. Org. Prep. Proced. Int. 2014, 46, 475 and references therein.

  11. Lonchakov, A. V.; Rakitin, O. A.; Gritsan, N. P.; Zibarev, A. V. Molecules 2013, 18, 9850.

    Article  CAS  Google Scholar 

  12. Hua, Y.; Wang, H.; Zhu, X.; Islam, A.; Han, L.; Qin, C.; Wong, W.-Y.;Wong, W.-K. Dyes Pigm. 2014, 102, 196.

    Article  CAS  Google Scholar 

  13. Wu, Z.; Li, X.; Li, J.; Hua, J.; Ågren, H.; Tian, H. Chem.– Asian J. 2014, 9, 3549.

  14. Wang, M.; Wang, H.; Yokoyama, T.; Liu, X.; Huang, Y.; Zhang, Y.; Nguyen, T.-Q.; Aramaki, S.; Bazan, G. C. J. Am. Chem. Soc. 2014, 136, 12576.

    Article  CAS  Google Scholar 

  15. Liu, X.; Sun, Y.; Hsu, B. B. Y.; Lorbach, A.; Qi, L.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2014, 136, 5697.

    Article  CAS  Google Scholar 

  16. Hua, Y.; He, J.; Zhang, C.; Qin, C.; Han, L.; Zhao, J.; Chen, T.; Wong, W.-Y.; Wong, W.-K.; Zhu, X. J. Mater. Chem. A 2015, 3, 3103.

    Article  CAS  Google Scholar 

  17. Wu, Y.; Zhu, W. Chem. Soc. Rev. 2013, 42, 2039.

    Article  Google Scholar 

  18. Ying, W.; Zhang, X.; Li, X.; Wu, W.; Guo, F.; Li, J.; Ågren, H.; Hua, J. Tetrahedron 2014, 70, 3901.

    Article  CAS  Google Scholar 

  19. Welch, G. C.; Perez, L. A.; Hoven, C. V.; Zhang, Y.; Dang, X.-D.; Sharenko, A.; Toney, M. F.; Kramer, E. J.; Nguyen, T.-Q.; Bazan, G. C. J. Mater. Chem. 2011, 21, 12700.

    Article  CAS  Google Scholar 

  20. Henson, Z. B.; Welch, G. C.; van der Poll, T.; Bazan, G. C. J. Am. Chem. Soc. 2012, 134, 3766.

    Article  CAS  Google Scholar 

  21. Budy, S. M.; Suresh, S.; Spraul, B. K.; Smith, D. W., Jr. J. Phys. Chem. C 2008, 112, 8099.

    Article  CAS  Google Scholar 

  22. Xia, P. F.; Feng, X. J.; Lu, J.; Tsang, S.-W.; Movileanu, R.; Tao, Y.; Wong, M. S. Adv. Mater. 2008, 20, 4810.

    Article  CAS  Google Scholar 

  23. Qin, P.; Zhu, H.; Edvinsson, T.; Boschloo, G.; Hagfeldt, A.; Sun, L. J. Am. Chem. Soc. 2008, 130, 8570.

    Article  CAS  Google Scholar 

  24. Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367.

    Article  CAS  Google Scholar 

  25. Bujak, P.; Kulszewicz-Bajer, I.; Zagorska, M.; Maurel, V.; Wielgus, I.; Pron, A. Chem. Soc. Rev. 2013, 42, 8895.

    Article  CAS  Google Scholar 

  26. Guo, F.; Liu, X.; Ding, Y.; Kong, F.; Chen, W.; Zhou, L.; Dai, S. RSC Adv. 2016, 6, 13433.

    Article  CAS  Google Scholar 

  27. Mao, J.; Zhang, X.; Liu, S.-H.; Shen, Z.; Li, X.; Wu, W.; Chou, P.-T.; Hua, J. Electrochim. Acta 2015, 179, 179.

    Article  CAS  Google Scholar 

  28. Arantes, C.; Scholz, M.; Schmidt, R.; Dehm, V.; Rocco, M. L. M.; Schöll, A.; Reinert, F.; Würthner, F. Appl. Phys. A: Mater. Sci. Process. 2012, 108, 629.

    Article  CAS  Google Scholar 

  29. Akkuratov, A. V.; Troshin, P. A. Polym. Sci., Ser. B 2014, 56, 414. [Vysokomolekul. Soedin., Ser. B 2014, 56, 371.]

  30. Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R.; Belletête, M.; Durocher, G.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2008, 130, 732.

    Article  CAS  Google Scholar 

  31. Li, Z. H.; Wong, M. S. Org. Lett. 2006, 8, 1499.

    Article  CAS  Google Scholar 

  32. Wu, Z.; An, Z.; Chen, X.; Chen, P. Org. Lett. 2013, 15, 1456.

    Article  CAS  Google Scholar 

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This work was performed with financial support from the Russian Science Foundation (project RNF 15-13-10022).

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Correspondence to Oleg A. Rakitin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 608–614

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Knyazeva, E.A., Chmovzh, T.N., Ustimenko, O.O. et al. Suzuki cross-coupling reactions of 4,7-dibromo[1, 2, 5]selenadiazolo[3,4-c]pyridine – a path to new solar cell components. Chem Heterocycl Comp 53, 608–614 (2017). https://doi.org/10.1007/s10593-017-2099-4

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  • DOI: https://doi.org/10.1007/s10593-017-2099-4

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