A series of lanthanide(III) complexes based on the new chiral ligand L, which contains 1,10-phenanthroline and (–)-menthol fragments, namely [LnL₂(NO₃)₃] (Ln = Eu (1), Gd (2), Tb (3), Dy (4)), have been synthesized and structurally characterized. Complexes 1–4 are isostructural and crystallize in the non-centrosymmetric space group P4₁2₁2. The mononuclear complexes comprise a 10-coordinate Ln³⁺ ion with two bidentate N,N-donor ligands (L) and three bidentate chelating nitrate groups. The magnetic properties of complexes 1–4 are determined mainly by the Ln³⁺ ions. In the case of complexes 3 and 4, significant anisotropy results in nonlinear field dependences of magnetization at low temperature. Complexes 1, 3 and 4 exhibit metal-centered red (Eu³⁺), green (Tb³⁺) and yellow (Dy³⁺) luminescence, respectively, whereas complex 2 displays blue ligand-based luminescence in the solid state at room temperature. The luminescence quantum yield for the solid samples increases in the order 4 < 2 ≈ 3 < 1. The europium(III) complex shows long luminescence lifetimes (up to 1750 μs) and a very high quantum yield (φ_f = 0.87); these make this compound promising for application in sensing and optoelectronics.

Mononuclear zinc(II) and cadmium(II) complexes, ZnLCl₂ (1), CdLCl₂ (2), ZnL¹Cl₂·2H₂O (3), and CdL¹Cl₂·2H₂O (4), with chiral ligands containing a 2,2′-bipyridine moiety and natural terpene (+)-limonene (L) or (+)-3-carene (L¹) moieties were synthesized. In these complexes the L and L¹ ligands are shown to coordinate Zn²⁺ and Cd²⁺ ions through the 2,2′-bipyridine moiety. The acetamide group of the ligands interacts with M²⁺ ions by forming N⋯M²⁺ and CO⋯M²⁺ contacts and N–H⋯Cl hydrogen bonds with coordinated Cl⁻ ions. In solutions the complexes have several conformers differing by the degree of the turn of the acetamide moiety relative to the ligand core and the type of its interaction with the coordination core. The ligands and complexes exhibit luminescence with the quantum yield increasing in the order: ligand < cadmium(II) complex < zinc(II) complex. The complexes 3 and 4 demostrate excitation wavelength independent single-channel fluorescence. As opposed to 3 and 4, the complexes 1 and 2 demonstrate excitation wavelength dependent emission with nanosecond and microsecond lifetimes of the excited states. According to our TD-DFT calculations, an interplay of ligand centered and halide to ligand transitions facilitates two deactivation channels in 1 and 2: S₁–S₀ and T₁–S₀.

Reaction of pinocarvone oxime with enamines and FeCl₃ or CuCl₂ resulted in annulation of nopinane carbon frame with pyridine and regioselective formation of chiral nopinane-annelated pyridines in 20–39% yields. Chemical structure of the pyridine derivatives were proved by precise NMR study.