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Thiophene, also known as thiacyclopentadiene, thiole or thiofuran, is a five-membered sulfur containing heterocyclic aromatic compound. Thiophene and its derivatives occur in natural deposits, and function as analogues of furans and pyrroles. Thiophenes undergo a large number of substitution reactions. Thiophene does not behave like thioethers, for example, the sulfur atom in a thiophene resists alkylation and oxidation. While the sulfur atom is relatively unreactive, carbon atoms alpha to sulfur are highly susceptible to attack by electrophiles. Halogens react with thiophenes to give 2-halothiophenes followed by 2,5-dihalo derivatives. In addition to their reactivity towards electrophiles, thiophenes can also be lithiated.
The thiophene core is used as building blocks in many agrochemicals and pharmaceuticals. Thiophene is a well-known bioisostere for benzene and hence finds extensive use in drug design and discovery to enhance activity or reduce toxicity without making significant structural changes. Furthermore, it is used as an additive of photoluminescent materials and pigments. In addition, it is also adopted as a raw material and intermediate in the chemical industry. Polymerized thiophenes on oxidation exhibit good electrical conducting properties through extensive delocalization of electrons and hence are called synthetic metals.