Synthesis and Properties of Benzobis(thiadiazole)s with Nonclassical π-Electron Ring Systems

Synthesis and applications of difluorobenzothiadiazole based conjugated polymers for organic photovoltaics

“…A 5 mm broadband probe was used for acquiring 13 C NMR spectra. CFCl 3 was used as an internal standard (0 ppm) for the 19 F NMR measurements. Gel permeation chromatography (GPC) (Waters Breeze HPLC system with 1525 Binary HPLC Pump and 2414 Differential Refractometer) was used for measuring the molecular weight and polydispersity index at 40 C. Chlorobenzene was used as eluent and commercial polystyrenes were used as standard.…”

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

“…12 A re-investigation of the synthesis of 1,2,5-thiadiazole-3,4-carbonitrile (10) from diaminomaleonitrile showed that the most probable intermediate is monosulfinylamine 11, which eliminates water by the action of hydrogen chloride formed in the first step of the reaction; 13 In many cases, employing an organic base allows the reaction temperature to be reduced to room temperature, or to 0 • C, avoiding undesirable side processes. Usually triethylamine [14][15][16][17][18][19] or pyridine [20][21][22][23][24][25] in inert solvents such as dichloromethane, benzene, or chloroform were used. Typical examples were given in Scheme 3.…”

“…Reaction of aromatic and heteroaromatic ortho-diamines and selenium dioxide was conducted in solid state, 204,205 in ethanol, 20,[206][207][208][209][210][211][212] in acetic anhydride, 213 and even in water. [214][215][216] Typical examples of fused 1,2,5-selenadiazoles prepared are given in Figure 6 (solvents used and yields of selenadiazoles are shown below the formulae).…”

“…Reduction of dinitrobenzenes 187 with tin in hydrochloric acid 206 or with iron dust in acetic acid 20 gave the corresponding diamines 188. The treatment of aromatic 1,2-diamines 188 with selenium dioxide led to selenadiazoles 189, as illustrates above (Scheme 95).…”

Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

“…If we consider intermolecular heteroatom interactions as connection tools, various types of heterocycles can be applied to molecular building blocks. We have synthesized unique molecules containing two fused 1,2,5-thiadiazole rings, benzobis(thiadiazole) [8] and bi(thiadiazolopyridylidene) [9] derivatives, so far. One-dimensional supramolecular tape structures linked by short intermolecular SÁÁÁN heteroatom interactions at the 1,2,5-thiadiazole rings were observed in their crystalline state.…”