Cyclopentathiadiazines, Cyclohepta‐ and Cyclopentadithiazoles: New Materials and a Rich Heterocyclic Chemistry of Cyclic Enaminonitriles

Abstract

Keywords: Sulfur-nitrogen heterocycles / Materials science / Liquid crystals / Radicals / Fused-ring systems 3-Amino-1H-indene-2-carbonitrile and 2-amino-3H-indene-1-carbonitrile reacted with SCl 2 , iBu 3 N and NCS to give benzocyclopenta[1,2,6]thiadiazines, and whilst 2-aminocyclopent-1-enecarbonitrile gave, under the same conditions, a cyclopenta[1,2,6]thiadiazine, its reaction with mixtures of S 2 Cl 2 , SCl 2 and iBu 3 N under different conditions gave, selectively, an isothiazolo [3,4-d]

5,5′-Bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione

“…The targeted bithiadiazine oligomer was 5,5′-bis[5-(9-decyl-9H-carbazol-3-yl)thien-2-yl]-4H,4′H-[3,3′-bi(1,2,6-thiadiazine)]-4,4′-dione (7), which contained the thiophene-carbazole motif, which was suitable as a donor unit for the D-A-D functional small molecule. Oligomer 7 could be directly compared with the respective monothiadiazine oligomer 4 (Figure 1) which gave a PCE of ~2% [15].…”

“…Non-oxidized 4H-1,2,6-thiadiazines are rare heterocycles. Nevertheless, interesting properties and applications of various analogues have appeared: selected 3-chloro-5-substituted-4H-1,2,6-thiadiazines display plant antifungal activity [1][2][3][4][5], whereas some fused analogues were studied as examples of "extreme quinoids" with ambiguous aromatic character [6], while others displayed liquid crystalline properties or behaved as near-infrared dyes [7,8]. Furthermore, selected 4H-1,2,6-thiadiazines were proposed as radical anion precursors for molecule-based magnetic and conducting materials [9], while π-conjugated polymers of 1,2,6-thiadiazines were proposed as potentially stable alternatives to the superconductor poly(sulfur nitride) (SN) x by both Woodward [10] and Rees [11][12][13].…”

3-Chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one

“…The elemental analysis was run by the London Metropolitan University Elemental Analysis Service. The compound 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) was prepared according to the literature [19]. 1632s, 1501w, 1439m, 1395s, 1373w, 1358w, 1339w, 1289w, 1271w, 1238w, 1175m, 1090w, 1015m, 939w, 856m, 843w, 822m Funding: Cyprus Research Promotion Foundation (Grants: ΣTPATHII/0308/06, NEKYP/0308/02 ΥΓEIA/0506/19 and ENIΣX/0308/83).…”

“…Non-oxidized 4H-1,2,6-thiadiazines are a rare class of heterocycles. However, recent interest in their properties and applications has fueled the development of their chemistry: many 3-chloro-5-substituted-4H-1,2,6-thiadiazines show plant antifungal activity [1][2][3][4][5], whereas several fused analogues were studied as examples of "extreme quinoids" with ambiguous aromatic character [6], and others display liquid crystalline properties or behave as near-infrared dyes [7,8]. Moreover, selected 4H-1,2,6-thiadiazines were proposed as radical anion precursors for molecule-based magnetic and conducting materials [9], while both Woodward [10] and Rees [11][12][13] proposed π-conjugated polymers of 1,2,6-thiadiazines as potentially stable alternatives to the superconductor poly(sulfur nitride) (SN) x .…”

5,5′-Thiobis(3-methoxy-4H-1,2,6-thiadiazin-4-one)

“…4H-1,2,6-thiadiazines are a class of heterocycles that do not occur in nature but have interesting applications: some 5-substituted 3-chloro-4H-1,2,6-thiadiazines show plant antifungal activity [1][2][3][4][5], while others display liquid crystalline or near-infrared dye behavior [6,7]. Moreover, certain 4H-1,2,6-thiadiazines were proposed to be precursors to radical anions for organic magnetic and conducting materials [8].…”