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3-Cyano-2-(dicyano)methylene-4-methyl-2,5-dihydrofurans in the synthesis of nonlinear-optical chromophores (minireview)

  • HETEROCYCLES IN FOCUS
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Chemistry of Heterocyclic Compounds Aims and scope

This minireview reflects the most significant advances in the synthesis of promising nonlinear-optical chromophores over the last 5–10 years. We focus on the studies of chromophores combining an electron-donating moiety with an electron-withdrawing 3-cyano-2-(dicyano)methylene-2,5-dihydrofuran-4-yl group through a linker containing a polyene motif or one to two five-membered heterocycles.

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References

  1. (a) Guenter, P. Nonlinear Optical Effects and Materials; Springer, 2002, 495 p. (b) Dalton, L. R.; Sullivan, P. A.; Bale, D. H. Chem. Rev. 2010, 110, 25.

  2. (a) Melikian, G.; Rouessac, F.; Alexandre, C. Synth. Commun. 1995, 25, 3045. (b) Villemin, D.; Liao, L. Synth. Commun. 2001, 31, 1771. (c) Zhang, T.; Guo, K. P.; Qiu, L.; Shen, Y. Synth. Commun. 2006, 36, 1367. (d) Moerner, W. E.; Twieg, R. J.; Kline D. W.; He, M. US Patent 20070134737. (e) Avetisyan, A. A.; Alvandzhyan, A. G.; Avetisyan, K. S. Russ. J. Org. Chem. 2009, 45, 1871. [Zh. Org. Khim. 2009, 45, 1872.] (f) Jen, K.-Y.; Jang, S.; Kang J.-W.; Luo, J.; Chen, B.; Liu, S.; Dalton L. R. US Patent 7425643. (g) He, M.; Leslie, T. M.; Sinicropi, J. A. Chem. Mater. 2002, 14, 2393.

  3. (a) Xua, H.; Zhanga, M.; Zhanga, A.; Denga, G.; Si, P.; Huanga, H.; Penga, C.; Fub, M.; Liua, J.; Qiua, L.; Zhena, Z.; Boa, S.; Liua, X. Dyes Pigm. 2014, 102, 142. (b) Zhou, T.; Liu, J.; Deng, G.; Wu, J.; Bo, S.; Qiu, L.; Liu, X.; Zhen, Z. Mater. Lett. 2013, 97, 117. (c) Wu, J.; Liu, J.; Zhou, T.; Bo, S.; Qiu, L.; Zhen, Z.; Liu, X. RSC Adv. 2012, 2, 1416.

  4. (a) Zhang, C.; Dalton, L. R. Chem. Mater. 2001, 13, 3043. (b) Cheng, Y.-J.; Luo, J.; Hau, S.; Bale, D. H.; Kim, T.-D.; Shi, Z.; Lao, D. B.; Tucker, N. M.; Tian, Y.; Dalton, L. R.; Reid, P. J.; Jen, A. K-Y. Chem. Mater. 2007, 19, 1154. (c) He, M.; Leslie, T.; Garner, S.; DeRosa, M.; Cites, J. J. Phys. Chem. B 2004, 108, 8731. (d) Luo, J.; Huang, S.; Cheng, Y. J.; Kim, T. D.; Shi, Z.; Zhou, X. H.; Jen, A. K. Y. Org. Lett. 2007, 9, 4471. (e) Luo, J.; Cheng, Y.-J.; Kim, T.-D.; Hau, S.; Jang, S.-H.; Shi, Z.; Zhou, X.-H.; Jen, A. K.-Y. Org. Lett. 2006, 8, 1387. (f) Cheng, Y.-J.; Luo, J.; Huang, S.; Zhou, X.; Shi, Z.; Kim, T.-D.; Bale, D. H.; Takahashi, S.; Yick, A.; Polishak, B. M.; Jang, S.-H.; Dalton, L. R.; Reid, P. J.; Steier, W. H.; Jen, A. K.-Y. Chem. Mater. 2008, 20, 5047. (g) Zhou, X-H.; Luo, J.; Davies, J. A.; Huanga, S.; Jen, A. K. Y. J. Mater. Chem. 2012, 22, 16390.

  5. (a) Wu, J.; Bo, S.; Liu, J.; Zhou, T.; Xiao, H.; Qiu, L.; Zhen, Z.; Liu, X. Chem. Commun. 2012, 48, 9637. (b) Bhuiyan, M. D. H.; Gainsford, G. J.; Kutuvantavida, Y.; Quilty, J. W.; Kay, A. J.; Williams, G. V. M.; Waterland, M. R. Mol. Cryst. Liq. Cryst. 2011, 548, 272.

  6. (a) Wang, H.; Liu, F.; Yang, Y.; Xu, H.; Peng, C.; Bo, S.; Zhen, Z.; Liu, X.; Qiu, L. Dyes Pigm. 2015, 112, 42. (b) Wu, J.; Peng, C.; Xiao, H.; Bo, S.; Qiu, L.; Zhen, Z.; Liu, X. Dyes Pigm. 2014, 104, 15. (c) Yang, Yu.; Liu, F.; Wang, H.; Zhang, M.; Xu, H.; Bo, S.; Liu, J.; Qiu, L.; Zhena, Z.; Liu, X. Phys. Chem. Chem. Phys. 2014, 16, 20209.

  7. (a) Robinson, B. H.; Dalton, L. R.; Harper, A. W.; Ren, A.; Wang, F.; Zhang, C.; Todorova, G.; Lee, M.; Aniszfeld, R.; Garner, S.; Chen, A.; Steier, W. H.; Houbrecht, S.; Persoons, A.; Ledoux, I.; Zyss J.; Jen, A. K. Y. Chem. Phys. 1999, 245, 35. (b) Liao, Yi; Anderson, C. A.; Sullivan, P. A.; Akelaitis, A. J. P.; Robinson, B. H.; Dalton, L. R. Chem. Mater. 2006, 18, 1062.

  8. Liu, F.; Wang, H.; Yang, Y.; Xu, H.; Yang, D.; Bo, S.; Liu, J.; Zhen, Z.; Liu, X.; Qiu, L. Dyes Pigm. 2015, 114, 196.

    Article  CAS  Google Scholar 

  9. Liu, F.; Wang, H.; Yang, Y.; Xu, H.; Zhang, M.; Zhang, A.; Bo, S.; Zhen, Z.; Liu, X.; Qiu, L. J. Mater. Chem. C 2014, 2, 7785.

    Article  CAS  Google Scholar 

  10. (a) Hammond, S. R.; Clot, O.; Firestone, K. A.; Bale, D. H.; Lao, D.; Haller, M.; Phelan, G. D.; Carlson, B.; Jen, A. K.-Y.; Reid, P. J.; Dalton, L. R. Chem. Mater. 2008, 20, 3425. (b) Akelaitis, A. J. P.; Olbricht, B. C.; Sullivan, P. A.; Liao, Y.; Lee, S. K.; Bale, D. H.; Lao, D. B.; Kaminsky, W.; Eichinger, B. E.; Choi, D. H.; Reid, P. J.; Dalton, L. R. Opt. Mater. 2008, 30, 1504.

  11. Zhang, A.; Xiao, H.; Cong, S.; Zhang, M.; Zhang, H.; Bo, S.; Wang, Q.; Zhen, Z.; Liu, X. J. Mater. Chem. C 2015, 3, 370.

    Article  CAS  Google Scholar 

  12. Levitskaya, A. I.; Kalinin, A. A.; Fominykh, O. D.; Balakina, M. Yu. Comput. Theor. Chem. 2015, 1074, 91.

    Article  CAS  Google Scholar 

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This work was performed with a partial financial support from the Russian Foundation for Basic Research (project No. 15-03-03048-a).

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 Arbuzova St., Kazan, 420088, Russia

    Sirina M. Sharipova & Alexey A. Kalinin

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  1. Sirina M. Sharipova
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  2. Alexey A. Kalinin
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Correspondence to Alexey A. Kalinin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 36–38

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Sharipova, S.M., Kalinin, A.A. 3-Cyano-2-(dicyano)methylene-4-methyl-2,5-dihydrofurans in the synthesis of nonlinear-optical chromophores (minireview). Chem Heterocycl Comp 53, 36–38 (2017). https://doi.org/10.1007/s10593-017-2017-9

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  • DOI: https://doi.org/10.1007/s10593-017-2017-9

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