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Substituent Effect on the Structure and Photophysical Properties of Phenylamino- and Pyridylamino-2,1,3-Benzothiadiazoles

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Abstract

4-Bromo-7-phenylamino-2,1,3-benzothiadiazole (1) and 4-bromo-7-(3-pyridylamino)-2,1,3-benzo thiadiazole (2) are synthesized. Their crystal structure and photophysical properties are studied in comparison with the known phenylamino- and pyridylamino-derivatives of 2,1,3-benzothiadiazole. It is found that the aryl substituent and noncovalent interactions affect the absorption band positions and emission in a solid and a solution. It is shown that under the mechanical action on polycrystalline samples of compounds 1 and 2 a hypsochromic shift of the emission band occurs, which indicates the weakening of noncovalent intermolecular interactions.

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References

  1. N. A. Pushkarevsky, E. A. Chulanova, L. A. Shundrin, A. I. Smolentsev, G. E. Salnikov, E. A. Pritchina, A. M. Genaev, I. G. Irtegova, I. Y. Bagryanskaya, S. N. Konchenko, N. P. Gritsan, J. Beckmann, and A. V. Zibarev. Chem. Eur. J., 2019, 25, 806.

    Article  CAS  Google Scholar 

  2. E. A. Chulanova, E. A. Pritchina, L. A. Malaspina, S. Grabowsky, F. Mostaghimi, J. Beckmann, I. Y. Bagryanskaya, M. V. Shakhova, L. S. Konstantinova, O. A. Rakitin, N. P. Gritsan, and A. V. Zibarev. Chem. Eur. J., 2017, 23, 852.

    Article  CAS  Google Scholar 

  3. E. A. Chulanova, N. A. Semenov, N. A. Pushkarevsky, N. P. Gritsan, and A. V. Zibarev. Mendeleev Commun., 2018, 28, 453.

    Article  CAS  Google Scholar 

  4. A. Abbas, J. J. Pillai, K. Sreekumar, R. Joseph, and C. S. Kartha. Opt. Mater., 2018, 84, 813.

    Article  CAS  Google Scholar 

  5. V.J. Rodrigues de Oliveira, E. Assunção da Silva, M. L. Braunger, H. Awada, H. de Santana, R. C. Hiorns, C. Lartigau-Dagron, and C. de Almeida Olivati. J. Mol. Liq., 2018, 268, 114.

    Article  CAS  Google Scholar 

  6. T. S. Sukhikh, D. S. Ogienko, D. A. Bashirov, and S. N. Konchenko. Russ. Chem. Bull., 2019, 4, 651.

    Article  Google Scholar 

  7. T. S. Sukhikh, D. A. Bashirov, D. S. Ogienko, N. V. Kuratieva, P. S. Sherin, M. I. Rakhmanova, E. A. Chulanova, N. P. Gritsan, S. N. Konchenko, and A. V. Zibarev. RSC Adv., 2016, 6, 43901.

    Article  CAS  Google Scholar 

  8. E. A. Knyazeva and O. A. Rakitin. Russ. Chem. Rev., 2016, 85, 1146.

    Article  CAS  Google Scholar 

  9. B. A. D. Neto, P. H. P.R. Carvalho, and J. R. Correa. Acc. Chem. Res., 2015, 48, 1560.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. O. A. Rakitin and A. V. Zibarev. Asian J. Org. Chem., 2018, 7, 2397.

    Article  CAS  Google Scholar 

  12. E. A. Knyazeva and O. A. Rakitin. Chem. Heterocyclic Compounds, 2017, 53, 855.

    Article  CAS  Google Scholar 

  13. T. N. Chmovzh, E. A. Knyazeva, L. V. Mikhalchenko, I. S. Golovanov, S. A. Amelichev, and O. A. Rakitin. Eur. J. Org. Chem., 2018, 2018, 5668.

    Article  CAS  Google Scholar 

  14. N. T. Chmovzh, A. E. Knyazeva, A. K. Lyssenko, V. V. Popov, and A. O. Rakitin. Molecules, 2018, 23, 2576.

    Article  Google Scholar 

  15. A. A. R. Mota, J. R. Correa, L. P. de Andrade, J. A. F. Assumpção, G. A. de Souza Cintra, L. H. Freitas-Junior, W. A. da Silva, H. C. B. de Oliveira, and B. A. D. Neto. ACS Omega, 2018, 3, 3874.

    Article  CAS  Google Scholar 

  16. F. F. D. Oliveira, D. C. B. D. Santos, A. A. M. Lapis, J. R. Corrêa, A. F. Gomes, F. C. Gozzo, P. F. Moreira, V. C. de Oliveira, F. H. Quina, and B. A. D. Neto. Bioorg. Med. Chem. Lett., 2010, 20, 6001.

    Article  CAS  Google Scholar 

  17. X. Han, Z. Wang, Q. Cheng, X. Meng, D. Wei, Y. Zheng, J. Ding, and H. Hou. Dyes and Pigments, 2017, 145, 576.

    Article  CAS  Google Scholar 

  18. Q. Ye, S. Chen, D. Zhu, X. Lu, and Q. Lu. J. Mater. Chem. B, 2015, 3, 3091.

    Article  CAS  Google Scholar 

  19. B. A. D. Neto, P. H. P. R. Carvalho, D. C. B. D. Santos, C. C. Gatto, L. M. Ramos, N. M. D. Vasconcelos, J. R. Corrêa, M. B. Costa, H. C. B. de Oliveira, and R. G. Silva. RSC Adv., 2012, 2, 1524.

    Article  CAS  Google Scholar 

  20. F. Ni, Z. Wu, Z. Zhu, T. Chen, K. Wu, C. Zhong, K. An, D. Wei, D. Ma, and C. Yang. J. Mater. Chem. C, 2017, 5, 1363.

    Article  CAS  Google Scholar 

  21. J. Wu, G. Lai, Z. Li, Y. Lu, T. Leng, Y. Shen, and C. Wang. Dyes and Pigments, 2016, 124, 268.

    Article  CAS  Google Scholar 

  22. C. Gu, D. Liu, J. Wang, Q. Niu, C. Gu, B. Shahid, B. Yu, H. Cong, and R. Yang. J. Mater. Chem. A, 2018, 6, 2371.

    Article  CAS  Google Scholar 

  23. C. Rodríguez-Seco, S. Biswas, G. D. Sharma, A. Vidal-Ferran, and E. Palomares. J. Phys. Chem. C, 2018, 122, 13782.

    Article  Google Scholar 

  24. H. Sakurai, M. T. S. Ritonga, H. Shibatani, and T. Hirao. J. Org. Chem., 2005, 70, 2754.

    Article  CAS  Google Scholar 

  25. P. Kubelka. J. Opt. Soc. Am., 1948, 38, 448.

    Article  CAS  Google Scholar 

  26. Bruker AXS Inc. APEX2 (Version 2.0), SAINT (Version 8.18c), and SADABS (Version 2.11), Bruker Advanced X-ray Solutions. Madison, Wisconsin, USA, 2000–2012.

    Google Scholar 

  27. G. M. Sheldrick. Acta Crystallogr., 2015, C71, 3.

    Google Scholar 

  28. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. J. Appl. Crystallogr., 2009, 42, 339.

    Article  CAS  Google Scholar 

  29. T. S. Sukhikh, D. S. Ogienko, D. A. Bashirov, N. V. Kurat’eva, A. I. Smolentsev, and S. N. Konchenko. Russ. J. Coord. Chem., 2019, 45, 30.

    Article  CAS  Google Scholar 

  30. M. T. Ritonga, H. Shibatani, H. Sakurai, T. Moriuchi, and T. Hiaro. Heterocycles, 2006, 68, 829.

    Article  CAS  Google Scholar 

  31. D. A. Bashirov, T. S. Sukhikh, N. V. Kuratieva, E. A. Chulanova, I. V. Yushina, N. P. Gritsan, S. N. Konchenko, and A. V. Zibarev. RSC Adv., 2014, 4, 28309.

    Article  CAS  Google Scholar 

  32. T. S. Sukhikh, V. Y. Komarov, S. N. Konchenko, and E. Benassi. Polyhedron, 2018, 139, 33.

    Article  CAS  Google Scholar 

  33. A. D. Laurent, Y. Houari, P. H. P. R. Carvalho, B. A. D. Neto, and D. Jacquemin. RSC Adv., 2014, 4, 14189.

    Article  CAS  Google Scholar 

  34. T. S. Sukhikh, D. A. Bashirov, S. Shuvaev, V. Y. Komarov, N. V. Kuratieva, S. N. Konchenko, and E. Benassi. Polyhedron, 2018, 141, 77.

    Article  CAS  Google Scholar 

  35. T. S. Sukhikh, D. S. Ogienko, D. A. Bashirov, N. V. Kuratieva, V. Y. Komarov, M. I. Rakhmanova, and S. N. Konchenko. J. Coord. Chem., 2016, 69, 3284.

    Article  CAS  Google Scholar 

  36. J. Gierschner and S. Y. Park, J. Mater. Chem. C, 2013, 1, 5818.

    Article  CAS  Google Scholar 

  37. Z. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liu, and J. Xu. Chem. Soc. Rev., 2012, 41, 3878.

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to A.P. Zubareva for performing the elemental analysis.

Funding

The work was performed within the State Contract of the Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences for basic scientific research.

Author information

Authors and Affiliations

  1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. S. Sukhikh, R. M. Khisamov, D. A. Bashirov, N. V. Kuratieva & S. N. Konchenko

  2. Novosibirsk State University, Novosibirsk, Russia

    T. S. Sukhikh, R. M. Khisamov, D. A. Bashirov, L. M. Kovtunova, N. V. Kuratieva & S. N. Konchenko

  3. Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    L. M. Kovtunova

Authors
  1. T. S. Sukhikh
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  2. R. M. Khisamov
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  3. D. A. Bashirov
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  4. L. M. Kovtunova
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  5. N. V. Kuratieva
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  6. S. N. Konchenko
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Correspondence to T. S. Sukhikh.

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Russian Text © The Author(s), 2019, published in Zhurnal Strukturnoi Khimii, 2019, Vol. 60, No. 10, pp. 1736–1745.

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Sukhikh, T.S., Khisamov, R.M., Bashirov, D.A. et al. Substituent Effect on the Structure and Photophysical Properties of Phenylamino- and Pyridylamino-2,1,3-Benzothiadiazoles. J Struct Chem 60, 1670–1680 (2019). https://doi.org/10.1134/S0022476619100135

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  • DOI: https://doi.org/10.1134/S0022476619100135

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