A New Method for the Synthesis of Bromine-Containing Heterocyclic Compounds for Photovoltaic Polymers

  • D. Khrustalev Qaraghandy State Medical University, Gogol Street 40, Karaganda, Kazakhstan; National Laboratory Astana, Nazarbayev University, 53, Kabanbay Batyr Ave., Astana, Kazakhstan
  • A. Yedrissov National Laboratory Astana, Nazarbayev University, 53, Kabanbay Batyr Ave., Astana, Kazakhstan
  • Y. Shishlova Qaraghandy State Medical University, Gogol Street 40, Karaganda, Kazakhstan
  • O. Tyagunova Qaraghandy State Medical University, Gogol Street 40, Karaganda, Kazakhstan
  • B. Ilyassov National Laboratory Astana, Nazarbayev University, 53, Kabanbay Batyr Ave., Astana, Kazakhstan
  • A. Kurbanova National Laboratory Astana, Nazarbayev University, 53, Kabanbay Batyr Ave., Astana, Kazakhstan
Keywords: green bromination method, bromination, green chemistry, 4,4-dibromo-1,1-biphenyl, 4,7-dibromo-2,1,3-benzothiadiazole, 2-bromothiophene, 2,5-dibromothiophene

Abstract

With the development and improvement of systems for converting sunlight into electric and thermal energy, more and more work is emerging on the development of the newest and most promising direction in solar energy, namely the creation of solar cells based on photosensitive polymers. Recently the power conversion efficiency of organic photovoltaic (OPV) devices has overcome the barrier of 17%, and thus we can expect a new wave of scientific interest in the development of new, more efficient OPV devices. Unfortunately, during searching for highly efficient chemical structures of OPV polymers, the researchers missed an important point: all photovoltaic polymers consist of aromatic and heteroaromatic «building blocks», which, in turn, are synthesized based on outdated techniques using highly toxic, dangerous for life and environment precursors. The development of «green», environmentally friendly, economically viable methods for the synthesis of photovoltaic polymers and building blocks for their production, will make the energy obtained from OPV truly «green». In this work, we present an alternative, «green» method for synthesizing halogen-containing aromatic and heteroaromatic, expensive building blocks most commonly used in the synthesis of photovoltaic polymers, which can be used to obtain photovoltaic polymers of various structures. We present the original methods for the synthesis of 4,4-dibromo-1,1- biphenyl (1), 4,7-dibromo-2,1,3-benzothiadiazole (2), 2-bromothiophene (3) and 2,5-dibromothiophene (4). All these methods differ from the previously described routes by their simplicity and convenience of their implementation, the absence of corrosive and irritant reagents, good yield and compliance with the principles of «Green Chemistry».

References

(1). A. Sharma, D. Pathak, T. Wagner, J. Optoelectron. Adv. M. 16 (2014) 1257–1268.

(2). V.D. Mitchell, D.J. Jones, Polym. Chem. 9 (2018) 795–814. Crossref

(3). S. Li, L. Ye, W. Zhao, H. Yan, B. Yang, D. Liu, W. Li, H. Ade, J. Hou, J. Am. Chem. Soc. 140 (2018) 7159–7167. Crossref

(4). W. Zhao, S. Li, H. Yao, S. Zhang, Y. Zhang, B. Yang, J. Hou, J. Am. Chem. Soc. 139 (2017) 7148–7151. Crossref

(5). L. Meng, Y. Zhang, X. Wan, C. Li, X. Zhang, Y. Wang, X. Ke, Z. Xiao, L. Ding, R. Xia, R. Xia, H.-L. Yip, Y. Cao, Y. Chen, Science 361 (2018) 1094–1098. Crossref

(6). E.R. Rwenyagila, International Journal of Photoenergy, Article ID 1656512 (2017) 12 p. Crossref

(7). L. Lu, T. Zheng, Q. Wu, Chem. Rev. 115 (2015) 12666–12731. Crossref

(8). R.E. Buckles, N.G. Wheeler, Organic Syntheses, Coll. 4 (1963) p. 256.

(9). M. Sendur, A. Balan, D. Baran, B. Karabay, L. Toppare, Org. Electron. 11 (2010) 1877–1885. Crossref

(10). Ya. L. Gol’dfarb, A. A. Dudinov, V. P. Litvinov, Bulletin of the Academy of Sciences of the USSR, Division of chemical science 31 (1982) 2104– 2105. Crossref

(11). S. Adimurthy, G. Ramachandtiach, A. Bedekar, S. Ghosh, B.C. Ranu, B.C. Ranu, Green Chem. 8 (2006) 916-922. Crossref

(12). D. Prat, A. Wells, J. Hayler, H. Sneddon, C.R. McElroy, S.A. Shehada, P.J. Dunn, Green Chem. 18 (2016) 288–296. Crossref

(13). Jay A. Young, J. Chem. Educ. 78 (2001) 873. Crossref

(14). Jay A. Young, J. Chem. Educ. 78 (2001) 721. Crossref

(15). P.T. Anastas, J.C. Warner, Green Chemistry: theory and practice. Oxford University Press: New York, 1998, p.30.

Published
2019-02-20
How to Cite
[1]
D. Khrustalev, A. Yedrissov, Y. Shishlova, O. Tyagunova, B. Ilyassov, and A. Kurbanova, “A New Method for the Synthesis of Bromine-Containing Heterocyclic Compounds for Photovoltaic Polymers”, Eurasian Chem. Tech. J., vol. 21, no. 1, pp. 41-44, Feb. 2019.
Section
Articles