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Synthesis and Electrochemical and Spectroscopic Characterization of 4,7-diamino-1,10-phenanthrolines and Their Precursors
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SYSNO ASEP 0511369 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and Electrochemical and Spectroscopic Characterization of 4,7-diamino-1,10-phenanthrolines and Their Precursors Author(s) Nycz, J. E. (PL)
Wantulok, J. (PL)
Sokolová, Romana (UFCH-W) RID, ORCID, SAI
Pajchel, L. (PL)
Stankevič, M. (PL)
Szala, M. (PL)
Malecki, G. J. (PL)
Swoboda, D. (PL)Article number 4102 Source Title Molecules. - : MDPI
Roč. 24, č. 22 (2019)Number of pages 25 s. Language eng - English Country CH - Switzerland Keywords phenanthroline ; amination ; cyclic voltammetry Subject RIV CG - Electrochemistry OECD category Physical chemistry Method of publishing Open access Institutional support UFCH-W - RVO:61388955 UT WOS 000501529700091 EID SCOPUS 85074976739 DOI 10.3390/molecules24224102 Annotation 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.
Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2020 Electronic address http://hdl.handle.net/11104/0301652
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