Photochromic and Ionochromic Properties of N,N’Cyclic Azomethine Imines

Photochromic 5-phenylpyrazolidin-3-one-basedazomethine imines containing 2-benzylidene 1, 2-(3nitrobenzylidene) 2, 2-(4-nitrobenzylidene) 3, 2-((1H-imidazol-2-yl)methylene) 4, 2-(pyridin-2ylmethylene) 5, 2-(quinolin-2-ylmethylene) 6 and 2-((8-hydroxyquinolin-2-yl)methylene) 7 substituents were synthesized. All the compounds exist in the ring-opened O forms. Under irradiation with light of 365 nm, compounds 1-7 undergo thermally reversible isomerization into ring-closed bicyclic diaziridine isomers C. Azomethine imines 4-6 exhibit properties of ion-active molecular “off-on” switches of fluorescence when interacting with F- or AcO- anions. Compound 7 represents bifunctional chemosensor demonstrating a colorimetric “naked-eye” effect for Ni2+cation and complete fluorescence quenching in the presence of H+, F– and CN– ions.

Author(s) Details

Vladimir A. Bren
Institute of Physical and Organic Chemistry, Southern Federal University, Rostov on Don, Russian Federation.

Alexander D. Dubonosov
Federal Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Rostov on Don, Russian Federation.

Oksana S. Popova
Institute of Physical and Organic Chemistry, Southern Federal University, Rostov on Don, Russian Federation.

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