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Benzothiadiazoles

The two N atoms in Benzothiadiazole could possibly form intermolecular hydrogen bonding, leading to a more planar backbone. Benzothiadiazole is a strong electron-accepting molecular fragment. By fusing it with thiazole donor-acceptor dyes, near-infrared fluorescence was created. The benzothiadiazole ring is a useful n-type building block for designing electron-transport materials for organic and polymer light-emitting diodes (LEDs). Arene- and heteroarene-fused thiadiazoles have also found use in the design of low-band-gap materials for the construction of organic field-effect transmitters (OFETs), as stable organic radicals, and as one or two photon-absorbing materials for the design of nonlinear near-infrared (NIR) dyes. Benzothiadiazoles acting as the electron-accepting cores have been incorporated into dendrimer-type light-harvesting materials.

(2,1,3-benzothiadiazol-4-yl)methanesulfonamide

(2E)-N-[2-(6-fluoro-3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]-3-(2-methylphenyl)prop-2-enamide

(E)-N-[2-(3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]-2-phenylethene-1-sulfonamide

(2E)-N-[2-(3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)prop-2-enamide

1-(1,3-benzothiazol-2-yl)azetidin-3-yl 2,1,3-benzothiadiazole-5-carboxylate

[5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,2-oxazol-3-yl]methyl 2,1,3-benzothiadiazole-5-carboxylate

(5-phenyl-1,2-oxazol-3-yl)methyl 2,1,3-benzothiadiazole-5-carboxylate

[5-(thiophen-2-yl)-1,2-oxazol-3-yl]methyl 2,1,3-benzothiadiazole-5-carboxylate

1-({1-[1-(2,1,3-benzothiadiazole-4-sulfonyl)azetidin-3-yl]-1H-1,2,3-triazol-4-yl}methyl)pyrrolidin-2-one

1-(2,1,3-benzothiadiazole-5-carbonyl)-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]piperidine-4-carboxamide

1-(3,4-dimethylphenyl)-3-[2-(6-fluoro-3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]urea

1-(3-chlorophenyl)-3-[2-(3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]urea

1-(5-chloro-2-methoxyphenyl)-3-(6-fluoro-1,3-dimethyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-5-yl)urea

1-(5-chloro-2-methoxyphenyl)-3-[2-(6-fluoro-3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]urea

1-(4-methoxy-1,3-benzothiazol-2-yl)azetidin-3-yl 2,1,3-benzothiadiazole-5-carboxylate

1'-(2,1,3-benzothiadiazole-5-carbonyl)-3,4-dihydrospiro[1-benzopyran-2,3'-pyrrolidine]-4-one

1-(2H-1,3-benzodioxole-5-carbonyl)-N-(2,1,3-benzothiadiazol-4-yl)azetidine-3-carboxamide

1-(benzo[c][1,2,5]thiadiazol-5-yl)-1H-pyrrole-2,5-dione

1-[(4-chlorophenyl)methyl]-3-(6-fluoro-1,3-dimethyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-5-yl)urea

1-benzyl-3-(1,3-dimethyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-5-yl)urea

1-[1-(2,1,3-benzothiadiazole-5-carbonyl)piperidin-4-yl]-3-methyl-1,3-dihydro-2lambda6,1,3-benzothiadiazole-2,2-dione

1-[(4-bromophenyl)methyl]-3-methyl-1,3-dihydro-2lambda6,1,3-benzothiadiazole-2,2-dione

1-[(4-chlorophenyl)methyl]-3-[2-(3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]urea

1-[(3,4-dimethoxyphenyl)methyl]-3-[2-(6-fluoro-3-methyl-2,2-dioxo-1,3-dihydro-2lambda6,1,3-benzothiadiazol-1-yl)ethyl]urea