New approaches to the synthesis of 4,7-dichloro-1,10-phenanthrolines and their corresponding 9H-carbazol-9-yl-, 10H-phenothiazin-10-yl- and pyrrolidin-1-yl derivatives were developed. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, electronic absorption spectroscopy and multinuclear NMR in both solution and solid state including 15N CP/MAS NMR. The structures of 5-fluoro-2,9-dimethyl-4,7-di(pyrrolidin-1-yl)-1,10-phenanthroline (5d), 4,7-di(9H-carbazol-9-yl)-9-oxo-9,10-dihydro-1,10-phenanthroline-5-carbonitrile (6a) and 4,7-di(10H-phenothiazin-10-yl)-1,10-phenanthroline-5-carbonitrile (6b) were determined by single-crystal X-ray diffraction measurements. The nucleophilic substitutions of hydrogen followed by oxidation produced compounds 6a and 6b. The electrochemical properties of selected 1,10-phenanthrolines were investigated using cyclic voltammetry and compared with commercially available reference 1,10-phenanthrolin-5-amine (5l). The spatial distribution of frontier molecular orbitals of the selected compounds has been calculated by density functional theory (DFT). It was shown that potentials of reduction and oxidation were in consistence with the level of HOMO and LUMO energies.

Department of Analytical Chemistry and Biomaterials Faculty of Pharmacy Medical University of Warsaw Banacha 1 02 097 Warsaw Poland

Department of Organic Chemistry Marie Curie Sklodowska University 33 Gliniana St PL 20614 Lublin Poland

Institute of Chemistry University of Silesia in Katowice ul Szkolna 9 PL 40007 Katowice Poland

Institute of Polymer and Dye Technology Lodz University of Technology Stefanowskiego 12 16 90 924 Lodz Poland

J Heyrovský Institute of Physical Chemistry of the Czech Academy of Sciences Dolejškova 3 18223 Prague Czech Republic

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