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One-pot Synthesis and Photophysical Studies of Α-cycloamino-substituted 5-aryl-2,2'-bipyridines

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Abstract

A series of α-cycloamine substituted 2,2’-bipyridines 3ae’-3ce’ was obtained via the one-pot approach based on ipso-substitution of a cyano-group in 1,2,4-triazines, followed by aza-Diels–Alder reaction in good yields. Photophysical properties, including fluorosolvatochromism, were studied for 3ae’-3ce’ and were compared with α-unsubstituted 2,2’-bipyridines. In addition, dipole moments differences in ground and excited states were calculated by both Lippert-Mataga equation and DFT studies and were compared to each other. The correlation between the size of cycloamine unit and the dipole moments differences value (based on Lippert-Mataga equation) was observed. In addition charge transfer indices (DCT, Λ, H and t) were calculated to demonstrate influence of molecular structure on the intramolecular charge transfer degree.

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Funding

This work was supported by the Russian Science Foundation grant # 19–73-10144-P (synthesis and primar photophysical studies), by the Russian Science Foundation grant # 21–13-00304 (fluorosolvatochromic studies), and by the RUDN University Strategic Academic Leadership Program (quantum chemical calculations).

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Authors and Affiliations

  1. Institute of Chemical Engineering, Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russia

    Mallikarjuna R. Guda, Maria I. Valieva, Dmitry S. Kopchuk, Rammohan Aluru, Albert F. Khasanov, Olga S. Taniya, Grigory V. Zyryanov & Brindaban C. Ranu

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya St. / 20 St., Ekaterinburg, 620137, Russia

    Maria I. Valieva, Dmitry S. Kopchuk & Grigory V. Zyryanov

  3. Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, Russia

    Alexander S. Novikov

  4. Joint Research Institute of Chemistry, Faculty of Physics, Mathematics and Natural Sciences, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Alexander S. Novikov

  5. School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700032, India

    Brindaban C. Ranu

Authors
  1. Mallikarjuna R. Guda
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  2. Maria I. Valieva
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  3. Dmitry S. Kopchuk
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  4. Rammohan Aluru
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  5. Albert F. Khasanov
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  6. Olga S. Taniya
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  7. Alexander S. Novikov
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  8. Grigory V. Zyryanov
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  9. Brindaban C. Ranu
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and photophysical studies were performed by M.R.Guda, M.I.Valieva, R.Aluru, A.F.Khasanov, quantum chemical calculations were performed by A.S.Novikov. Data interpretation was performed by A.F.Khasanov, D.S.Kopchuk, O.S.Taniya. Writing—original draft preparation was performed by A.F.Khasanov. Writing—review and editing were performed by D.S.Kopchuk and G.V.Zyryanov. Supervising by B.C.Ranu. All authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Albert F. Khasanov.

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Guda, M.R., Valieva, M.I., Kopchuk, D.S. et al. One-pot Synthesis and Photophysical Studies of Α-cycloamino-substituted 5-aryl-2,2'-bipyridines. J Fluoresc 34, 579–586 (2024). https://doi.org/10.1007/s10895-023-03304-1

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