A series of novel 3(5)-aryl/ferrocenyl-5(3)-phenothiazinylpyrazoles and pyrazolines were obtained by substituent-dependent regioselective condensation of the corresponding (E)-3-(2-alkyl-10H-phenothiazin-3-yl)-1-aryl/ferrocenylprop-2-en-1-one with hydrazine or methylhydrazine in acetic acid. The different propensity of the primary formed β-hydrazino adducts to undergo competitive retro-Mannich reaction was interpreted in terms of tautomerisation equilibrium constants calculated by DFT using a solvent model. The regioselectivity of the cyclisation reactions with methylhydrazine and the substituent-dependent redox properties of pyrazolines were also rationalized by comparative DFT calculations performed for simplified model molecules. On the effect of ultrasound-promoted oxidation with copper(II)nitrate phenothiazine-containing pyrazolines, enones and oxo-compounds were selectively transformed into sulfoxides. Only one sulfoxide enone was partially converted into an oxirane derivative. The structure of the novel products was determined by IR and NMR spectroscopy including COSY, HSQC, HMBC and DNOE measurements.

A comparative adsorption study was carried out for methylene blue (MB) and its 3,7-bis(N,N-(2-hydroxyethyl)amino)-phenothiazinium dye analog (MBI). Batch experiments employed aqueous solutions and commercial filter paper. Out of seven kinetic models tested by means of four quality statistical indicators, the pseudo-second-order, the double-exponential, and the bi-linear Weber–Morris equations were best fits. For both dyes, the process was described as a succession of two diffusion-controlled steps. The Freundlich isotherm was chosen from 11 models describing a variety of mechanism assumptions. Physisorption was considered responsible for the dye removal from liquid. Adsorption of MB is thermodynamically favored, whereas that of MBI is sterically hindered. Both processes are exothermic and exhibit reduced randomness at the S-L interface. The paper was found suitable for retaining MB but served rather filtration/purification purposes for MBI.