Hlp smart 1000

N,N-Dimethyldecylamine (90%, Sigma-Aldrich), 1,4-dibromobutene (99%, Sigma-Aldrich), 1,6-dibromohexane (96%, Sigma-Aldrich), 1,8-dibromooctane (98%, Sigma-Aldrich), 1,10-dibromodecane (97%, Sigma-Aldrich), 1,12-dibromododecane (98%, Sigma-Aldrich), acesulfame K (≥ 99%, Sigma-Aldrich), l-lactic acid (85%, Sigma-Aldrich), l-pyroglutamic acid (≥ 99%, Sigma-Aldrich), saccharin sodium hydrate (99%, Alfa Aesar), potassium hydroxide (85%, POCH), methanol, dimethyl sulfoxide, acetonitrile, acetone, 2-propanol, ethyl acetate, chloroform, toluene and hexane were purchased from Sigma-Aldrich and used without further purification. Water was deionized by demineralizer HLP Smart 1000 (Hydrolab).

Myristyltrimethylammonium bromide 99% from Sigma-Aldrich, Saint Louis, MO, USA. Stearyltrimethylammonium chloride (80% isopropanolic solution) and behenyltrimethylammonium chloride (80% isopropanolic solution) were purchased from KCI Limited, Chungnam, South Korea. Arquad 2HT (di(hydrogenated tallow)dimethylammonium chloride, 75% isopropanolic solution), Arquad C-35 (cocotrimethylammonium chloride, 35% aqueous solution) and didecyldimethylammonium chloride (40% aqueous solution) were obtained from Akzo-Nobel, Amsterdam, The Netherlands. Dioctyldimethylammonium chloride (99%) was purchased from CHEMOS GmbH, Altdorf, Germany. Cetyltrimethylammonium chloride (50% aqueous solution) was obtained from Stockmeier Chemie, Poznan, Poland. Iodosulfuron-methyl sodium salt (97%) was from Pestinova, Jaworzno, Poland. All solvents (methanol, DMSO, acetonitrile, acetone, isopropanol, ethyl acetate, chloroform, toluene, hexane) and potassium hydroxide were obtained from Avantor, Gliwice, Poland. Deionized water with conductivity <0.1 µS·cm⁻¹, was obtained from demineralizer Hydrolab HLP Smart 1000, Straszyn, Poland. All tetraalkylammonium halides were thoroughly dried at 50 °C for 48 h under reduced pressure (1–2 mbar) prior to the syntheses.

In the study, CuCl₂, CoCl₂, NiCl₂, dichloromethane CH₂Cl₂ (Chempur, Piekary Śląskie, Poland), NaCl (STANLAB, Lublin, Poland), cellulose triacetate (CTA, > 98%, Sigma-Aldrich, Poznań, Poland), and o-nitrophenyl octyl ether (ONPOE, Fluka, Buchs, Switzerland) were used. To synthesize 1-alkyl-1,2,4-triazoles (TRIA–n, n = 8, 9, 10, 11, 12, 14), the following compounds were used: sodium, 1,2,4-triazole and proper 1-bromoalkanes: 1-bromooctane, 1-bromononane, 1-bromodecane, 1-bromoundecane, 1-bromododecane (Sigma-Aldrich, Poznań, Poland), 1-bromotetradecane, and methanol (Chempur, Piekary Śląskie, Poland).
All reagents used were of analytical grade. Demineralised water was used to prepare water solutions (≤ 1 μS, HydroLab HLP Smart 1000 (HydroLab, Straszyn, Poland)).