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6‐Arylamino‐2,2′‐bipyridine “Push‐Pull” Fluorophores: Solvent‐Free Synthesis and Photophysical Studies
Author(s) -
Kopchuk Dmitry S.,
Krinochkin Alexey P.,
Starnovskaya Ekaterina S.,
Shtaitz Yaroslav K.,
Khasanov Albert F.,
Taniya Olga S.,
Santra Sougata,
Zyryanov Grigory V.,
Majee Adinath,
Rusinov Vladimir L.,
Chupakhin Oleg N.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800220
Subject(s) - stokes shift , chemistry , aniline , solvatochromism , fluorescence , solvent , pyridine , bipyridine , photochemistry , crystallography , organic chemistry , crystal structure , physics , quantum mechanics
This work describes a solvent‐free approach towards “push‐pull” fluorophores based on 5‐aryl‐2,2′‐bipyridines bearing the residues of various anilines at the α‐position of the edge pyridine cycle. We have also studied the possibility of varying (het)aromatic‐substituents at C5 position of the resulted 2,2′‐bipyridines as well as the substituents in the aniline residues. The structures of products were confirmed based on the 1 H and 13 C NMR spectroscopic data, mass spectrometry, elemental analysis and X‐ray diffraction analysis. The photophysical features of the synthesized compounds have been investigated. The fluorescence emission of two key compounds was studied in solvents by varying polarities. It was demonstrated that an increase in the solvent polarity led to an increase in the Stokes shift. The linear dependence of the Stokes shift of the fluorophores on the increasing of the solvent nature was demonstrated by using the Lippert–Mataga plot. The fluorescence quenching response of the fluorophores towards metal cations was also demonstrated.