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

Mallikarjuna R Guda; Maria I Valieva; Dmitry S Kopchuk; Rammohan Aluru; Albert F Khasanov; Olga S Taniya; Alexander S Novikov; Grigory V Zyryanov; Brindaban C Ranu

doi:10.1007/s10895-023-03304-1

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

J Fluoresc. 2024 Mar;34(2):579-586. doi: 10.1007/s10895-023-03304-1. Epub 2023 Jun 16.

Authors

Mallikarjuna R Guda¹, Maria I Valieva^{1

2}, Dmitry S Kopchuk^{1

2}, Rammohan Aluru¹, Albert F Khasanov³, Olga S Taniya¹, Alexander S Novikov^{4

5}, Grigory V Zyryanov^{1

2}, Brindaban C Ranu^{1

6}

Affiliations

¹ Institute of Chemical Engineering, Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russia.
² Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya St. / 20 St., Ekaterinburg, 620137, Russia.
³ Institute of Chemical Engineering, Ural Federal University, 19 Mira St., Ekaterinburg, 620002, Russia. a.f.khasanov@ya.ru.
⁴ Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, Russia.
⁵ 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.
⁶ School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700032, India.

PMID: 37326925
DOI: 10.1007/s10895-023-03304-1

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 (D_CT, Λ, H and t) were calculated to demonstrate influence of molecular structure on the intramolecular charge transfer degree.

Keywords: 2,2’-bipyridines; CT-indices; Cycloamines; DFT studies; Fluorosolvatochromism; Lippert-Mataga equation.

Grants and funding

19-73-10144-P/Russian Science Foundation