Metal-containing 2,2′:6′,2′′-terpyridine (terpy) compounds have applications in pharmaceutical production, where they have potential to facilitate aromatic carbon-hydrogen (C-H) fluorination. By modifying terpy ligands and reacting them with d8 metal centers, new inorganic complexes with tunable properties can be created. These compounds can then be manipulated to include other molecules in order to access different chemical properties, such as a change in the oxidation state of the metal center. Our laboratory has synthesized a series of phenyl terpy ligands (1) containing a systematic sequence of halogen R-groups in the 4 position of the phenyl ring. Various metal centers including Pd2+(2), Pt2+(3), and UO22+(4) were then introduced into these complexes. The 4-fluro terpy ligand (1a) was the primary ligand used for transition metal coordination, however, metal-containing derivatives of 4-chloro (1b) and 4-bromo (1c) and were also synthesized for each metal listed above. The 1a fluorine-containing terpy allowed for 19F NMR to be used as a measurement of the effect the metal center imparts on the terpy ligand. The introduction of the different metals caused a systematic change in the position of the fluorine peak on the 19F spectra. This effect was also observed in the 1H NMR and the gCOSY NMR. Further characterization was carried out using UV-Vis and fluorescence spectroscopy, which indicated the changes in the electronic properties of the systems. Future directions in this work may include interactions between two or more of the metal terpy compounds. By modifying the metal center, there is potential for the inclusion of two or more terpy ligands around a single metal center. Furthermore, the flat geometry of the terpy ligands allows for the addition of a flexible linker to join two metal terpy complexes. Once linked, potential interactions between the two metal centers may occur. After these multiple metal terpy complexes are successfully synthesized, further research can be done to gain insight into characteristics of the compounds. These compounds can then potentially be used for the creation of new drugs because of their ability to affect a variety of catalytic processes.

Systemic electronic effects of palladium, platinum and other metal-containing phenyl terpy complexes

256th National Meeting (2018)

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