A new intermediate for producing vinylsulfone-type reactive dyes was designed and synthesized. Two 4-step synthetic routes to the dye intermediate afforded an overall yield of 47 and 82 %, respectively. The structures of the intermediate and related compounds were characterized by 1H NMR, 13C NMR, IR, and mass spectrum.

A new chiral tetrathiafulvalene (TTF) derivative and related silyl-substituted 1,3-dithiole-2-(thi)one compounds were synthesized and characterized by 1H NMR, 13C NMR, MS and IR spectra. Single crystal structure of the silyl-substituted 1,3-dithiole-2-one revealed the high degree of conjugation of the five-membered ring moiety in the compound. The electrochemical properties of the new TTF derivative were studied by cyclic voltammetry and the results indicated that the electron-donating ability of the chiral TTF derivative was similar to that of BEDT-TTF. The ΔE value for the new TTF derivative was smaller than those for TTF and BEDT-TTF, indicative of decreased Coulombic repulsion in the dicationic redox state. Formation of charge-transfer (CT) complex between the new donor and electron acceptor 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was demonstrated.Electrochemical properties of a new chiral tetrathiafulvalene (TTF) derivative were studied by cyclic voltammetry. Formation of CT complex between the new donor and acceptor DDQ was demonstrated.

A new tetrathiafulvalene (TTF) derivative 2,3;6,7-bis[(2,2-dimethyl-2-silapropylene)dithio]-1,4,5,8-tetrathiafulvalene and the related silyl-substituted 1,3-dithiole-2-(thi)one were synthesized. Their structures were characterized by 1H NMR, 13C NMR, 29Si NMR, MS and IR spectra. Single crystal structure of the 1,3-dithiole-2-thione compound revealed the high degree of conjugation of the five-membered ring moiety in the DMIT compound. The electrochemical properties of the new TTF derivative were studied by cyclic voltammetry. The formation of charge-transfer complex between the new donor and acceptor DDQ was demonstrated.Graphical abstractA new tetrathiafulvalene (TTF) derivative and the related silyl-substituted 1,3-dithiole-2-(thi)one were synthesized and characterized by 1H NMR, 13C NMR, 29Si NMR, MS and IR spectra. Single crystal structure of the 1,3-dithiole-2-thione compound revealed the high degree of conjugation of the five-membered ring moiety in the DMIT compound. The electrochemical property of the new TTF derivative was studied by cyclic voltammetry. Formation of charge-transfer complex between the new donor and DDQ was demonstrated.Highlights► A silyl-substituted TTF and 1,3-dithiole-2-(thi)one were synthesized. ► Their structures were confirmed by NMR, MS and IR. ► Cyclic voltammetry of the new TTF derivative was determined. ► The formation of CT complex between the donor and DDQ was demonstrated.

Novel quaternary ammonium Gemini surfactants, which turned out to be ionic liquids due to the intermolecular hydrogen bonding formed from hydroxyl groups in the spacers, were synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectra. The surface properties of the Gemini surfactants were investigated by means of surface tension measurements. Surface tension parameters including surface excess concentration, Гcmc, surface area demand per molecule, Acmc, efficiency in surface tension reduction, pC20, the effectiveness of surface tension reduction, γcmc, critical micelle concentration, CMC, and standard free energy of micellization, ΔGads0 and ΔGmic0 were obtained. The results indicated that compared with those of their corresponding conventional single-chain surfactant counterparts, these novel Gemini surfactants exhibited lower CMC values and greater efficiency in lowering the surface tension of water. The foamability and foam stability of these Gemini surfactants decreased with the increase in the length of the spacer chain. Gemini surfactants with alkyl chains of moderate length (C12 or C14) showed the best foamability and the highest foam stability. Some of the Gemini surfactants exhibited antimicrobial activity against Gram-negative bacteria Escherichia coli.Graphical abstractNovel quaternary ammonium Gemini surfactants were synthesized. They turned out to be ionic liquids due to the intermolecular hydrogen bonding. Surface properties of the Gemini surfactants were investigated by means of surface tension measurements. Surface tension parameters including Гcmc, Acmc, pC20, γcmc, CMC, ΔGads0 and ΔGmic0 were obtained. The foamability and foam stability of the surfactants decreased with the increase of the spacer length. Gemini surfactants with alkyl chains of moderate length (C12 or C14) showed the best foamability and the highest foam stability. Some of the Gemini surfactants exhibited antimicrobial activity against Escherichia coli.Highlights► Novel quaternary ammonium Gemini surfactants were synthesized. ► They turned out to be ionic liquids. ► Their surface properties were investigated. ► Their foamability and foam stability were studied. ► Some of them exhibited antimicrobial activity.

A series of novel coumarin dyes (3–12) were designed and synthesized. The structures of the dyes were characterized by IR, 1H NMR, 13C NMR, 19F NMR, MS and single crystal X-ray diffraction. 3-(2-Benzoylhydrazonotrifluoroethyl)-7-(N,N-diethylamino)coumarin (11) could recognize Cu2+ and Ni2+ selectively in aqueous solution. Upon addition of Cu2+ or Ni2+ to 11 a blue shift or a bathochromatic shift of the absorption band was observed while the emission band blue-shifted with decrease in the fluorescence intensity. Upon addition of Cu2+ the color of the solution of 11 changed from orange to red. The results showed that 11 could be used as an optical chemosensor of Cu2+ and Ni2+.Highlights► Novel coumarin dyes were synthesized and characterized. ► A coumarin dye (11) could recognize Cu2+ and Ni2+ selectively in aqueous solution. ► Upon addition of Cu2+ the color of the coumarin solution changed from orange to red.

Ethylene trithiocarbonate reacted with dimethyl acetylenedicarboxylate to furnish tetramethyl thiopyran-4-spiro-2′-(1,3-dithiolane)-2,3,5,6-tetracarboxylate, a new thiopyran-4-spiro-2′-(1,3-dithiolane) heterocyclic compound, as the minor product together with the major product dimethyl 2-thioxo-1,3-dithiole-4,5-dicarboxylate. The new heterocycle was probably formed through a [2 + 2] cycloaddition between ethylene trithiocarbonate and dimethyl acetylenedicarboxylate followed by a 1,3-dipolar cycloaddition or [4 + 2] cycloaddition. Crystal structure of the new compound revealed that the thiopyran ring and 1,3-dithiolane moiety were perpendicular to each other.

Preparative chemical methods for the synthesis of 10 degradation or photodecomposition products of mestranol and ethinyl estradiol (EE) are described. The synthesized compounds are useful as reference materials and standards for pharmaceutical analysis of mestranol and EE as bulk chemical or in formulated product. New synthetic methods were presented and the known synthetic procedures were improved. Detailed structural characterization of the degradation or photodecomposition products of mestranol and EE and related compounds was reported.