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Perylene Dyes

 Perylene was a p-type organic semiconductor and it was known in the 1950s that the bromine-doped material showed electrical conductivity.1) In contrast to that, perylenetetracarboxylic dianhydride and perylenetetracarboxylic diimide derivatives are n-type organic semiconductors. The latter perylenetetracarboxylic derivatives (PDI or PBI) are important semiconducting materials, because n-type ones are relatively less known than p-type ones. In fact, PTCBI (3,4,9,10-perylenetetracarboxylic bisbenzimidazole) was an n-type organic semiconductor for a prototype of organic photovoltaics.2)
 Applications in organic electronics using PDI derivatives are organic light-emitting diode (OLED) materials3) and laser dyes4) thanks to their high fluorescent quantum efficiency and photochemical stability. PDIs with electron mobility larger than 0.1 cm2/Vs are also reported.5,6) An introduction of an alkyl group on the imido moiety (NR) produces soluble PDI derivatives, although they are poorly soluble in general.7) Recent research has proved direct alkylations at the meta positions (1,6,7,12-positions),8,9) and direct boronations at the ortho positions (2,5,8,11-positions)10) for PDIs. Halogenations at the meta positions are available, followed by various cross-coupling reactions11) and polymerizations12) providing PDI derivatives with diverse molecular structures and molecular weights.

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