Synthesis of Novel Phenanthroimidazole Based Beta-Diketone Compounds: Investigation of Their Spectroscopic Properties and Electrochemical Characterization.

Abstract

In this study, three new phenanthroimidazole based beta-biketone compounds containing different donor (methoxy and dodecyloxy) and acceptor (cyano) groups were synthesized. Spectroscopic and electrochemical properties of the synthesized compounds were studied. FTIR, ¹H-NMR, ¹³C-NMR, and LC-MS/MS were carried out for the structural analyses of the phenanthroimidazole derivatives. UV-vis absorption and emission studies were also carried out in the solvents with different polarities. High molar absorption coefficients and high Stokes' shift values were observed. The photostability of these derivatives was measured in all the solvents used. These values suggest that the derivatives could be used in fluorescence imaging applications for various biological and analytical purposes. Furthermore, the potential use of these molecules as electron transfer mediators for the electrochemical behavior of biological material was investigated. All the curves were also simulated using the most suitable equivalent Randles circuit. The charge-transfer resistance values varied depending on the donor and acceptor groups in the synthesized molecules. The Nyquist plots were evaluated, and it was observed that these molecules exhibit different resistance to electron transfer. These synthesized molecules can potentially be used as electron transfer mediators in the electrochemical detection of biological analytes.