Tetrazoles are doubly unsaturated five-membered aromatic heterocycles consisting of one carbon atom and four nitrogen atoms. Tetrazole derivatives are a major class of heterocyclic compounds that are important for medicinal chemistry and drug design because of their not only isosteric properties with carboxylic acid and amide moieties, but also metabolic stability and other beneficial physicochemical properties.
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.
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