Six new copper(II) complexes with 2,2′:6′,2′′-terpyridine (4′-Rⁿ-terpy) [1 (R¹ = furan-2-yl), 2 (R² = thiophen-2-yl), and 3 (R³ = 1-methyl-1H-pyrrol-2-yl)] and 2,6-di(thiazol-2-yl)pyridine derivatives (Rⁿ-dtpy) [4 (R¹), 5 (R²), and 6 (R³)] have been synthesized by a reaction between copper(II) chloride and the corresponding ligand. The complexes have been characterized by UV-vis and IR spectroscopy, and their structures have been determined by X-ray analysis. The antiproliferative potential of copper(II) complexes of 2,2′:6′,2′′-terpyridine and 2,6-di(thiazol-2-yl)pyridine derivatives towards human colorectal (HCT116) and ovarian (A2780) carcinoma as well as towards lung (A549) and breast adenocarcinoma (MCF7) cell lines was examined. Complex 1 and complex 6 were found to have the highest antiproliferative effect on A2780 ovarian carcinoma cells, particularly when compared with complex 2, 3 with no antiproliferative effect. The order of cytotoxicity in this cell line is 6 > 1 > 5 > 4 > 2 ≈ 3. Complex 2 seems to be much more specific towards colorectal carcinoma HCT116 and lung adenocarcinoma A549 cells. The viability loss induced by the complexes agrees with Hoechst 33258 staining and typical morphological apoptotic characteristics like chromatin condensation and nuclear fragmentation. The specificity towards different types of cell lines and the low cytotoxic activity towards healthy cells are of particular interest and are a positive feature for further developments. Complexes 1–6 were also tested in the oxidation of alkanes and alcohols with hydrogen peroxide and tert-butyl-hydroperoxide (TBHP). The most active catalyst 4 gave, after 120 min, 0.105 M of cyclohexanol + cyclohexanone after reduction with PPh₃. This concentration corresponds to a yield of 23% and TON = 210. Oxidation of cis-1,2-dimethylcyclohexane with m-CPBA catalyzed by 4 in the presence of HNO₃ gave a product of a stereoselective reaction (trans/cis = 0.47). Oxidation of secondary alcohols afforded the target ketones in yields up to 98% and TON = 630.

The synthesis and characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels–Alder reactions are described. D-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by ¹H and ¹³C NMR spectroscopy and by ESI-MS experiments, which confirmed their structures. In addition, the thermal data of the studied ionic liquids measured by differential scanning calorimetry and thermogravimetric analysis showed that these compounds tend to form a glass at temperatures in the range of −29 °C to −16 °C and are thermally stable from ambient temperature to at least 430 °C, most likely because of the presence of bis(trifluoromethylsulfonyl)imide anions. The performance of the ionic liquids in the model reaction of cyclopentadiene with diethyl maleate or methyl acrylate was investigated. The studied ionic liquids showed high activity even when present in catalytic amounts (4 mol% with respect to the dienophile). An increase in the number of hydroxyl groups present in the ionic liquid structure resulted in higher reaction rates.

The toxicity of six new Cu( ii ) complexes was evaluated in cancer derived cell lines. A model of competitive interaction of hydroxyl radicals with CH ₃ CN and RH in the catalyst cavity has been proposed.

Several 2,2′:6′,2′′-terpyridines substituted in the 4′-position were synthesized and their photophysical properties were investigated by absorption and photoluminescence spectroscopy in dilute solutions and solid state. The studies confirmed that the absorption and emission wavelengths, fluorescence quantum yields and lifetimes of 1-R^1–16 are strongly structure-related, demonstrating a decisive role of the nature of the substituent in determining the photophysical properties of 4′-functionalized terpyridines. Additionally, the density functional theory (DFT) calculations were performed for 1-R^1–16 to get insight into their electronic structure and spectroscopic properties.

Photophysics of [ReCl(CO)₃(4′-R-terpy-κ²N)].

A new family of herbicidal ionic liquids based on d -glucose and MCPA or 2,4-D anions has been synthesized and the physicochemical, surface active and herbicidal properties of the obtained salts were characterized.