Cleavage of the Se–Se bond in [2-{O(CH₂CH₂)₂NCH₂}C₆H₄]₂Se₂ (1) and [2-{MeN(CH₂CH₂)₂NCH₂}C₆H₄]₂Se₂ (2) by treatment with SO₂Cl₂, bromine or iodine (1 : 1 molar ratio) yielded [2-{O(CH₂CH₂)₂NCH₂}C₆H₄]SeX [X = Cl (3), Br (4), I (5)] and [2-{MeN(CH₂CH₂)₂NCH₂}C₆H₄]SeI (6). The compounds were characterized in solution by NMR spectroscopy (¹H, ¹³C, ¹⁵N, ⁷⁷Se, 2D experiments). The solid-state molecular structures of 1–3, 4·HBr, 5 and 6 were established by single crystal X-ray diffraction. In all cases T-shaped coordination geometries, i.e. (C,N)SeSe (1, 2), (C,N)SeX (3, 5, 6; X = halogen) or CSeBr₂ (4·HBr), were found. Supramolecular associations in crystals based on hydrogen contacts are discussed.

Lycopene, β-carotene and ω-fatty acids are major compounds in tomatoes with known antioxidant activity, capable of preventing health disorders. The identification of potential natural sources of antioxidants, extraction efficiencies and antioxidant activity assessments are essential to promote such products to be used in the food, pharmaceutical or cosmetic industries. This work presents four added-value products recovered from tomatoes: pigmented solid oleoresin, pigmented oil and two raw extracts from supercritical and Soxhlet extraction. Different parameters including the matrices of tomatoes, extraction methods, green solvents and operating parameters were varied to obtain extracts with different qualities. Extract analysis was performed using UV–VIS, FT–IR, GC–MS, Folin–Ciocalteu and DPPH methods. The highest-quality extract was the solid oleoresin obtained from pomace using supercritical CO₂ extraction at 450 bar, 70 °C and 11 kg/h: 1016.94 ± 23.95 mg lycopene/100 g extract, 154.87 ± 16.12 mg β-carotene/100 g extract, 35.25 ± 0.14 mg GAE/g extract and 67.02 ± 5.11% inhibition DPPH. The economic feasibility of the three extraction processes (1:10:100 kg dried pomace/batch as scalability criterion) was evaluated. The most profitable was the supercritical extraction process at the highest capacity, which produces pigmented solid oleoresin and oil with high content of lycopene valorized with a high market price, using natural food waste (pomace).