Diketo-pyrrolo-pyrrols

Diketo-pyrrolo-pyrrol, pigment for plastics, 7 367t... 

Zhang, X., Richter, L.J., Delongchamp, D.M., KUne, R.J., Hammond, M.R., Mcculloch, I., Heeney, M., Ashraf, R.S., Smith, J.N., Anthopoulos, X.D., Schroeder, B., Geerts,Y.H., Fischer, D.A., Toney, M.E, 2011. Molecular packing of high-mobility diketo pyrrolo-pyrrole polymer semiconductors with branched alkyl side chains. J. Am. Chem. Soc. 133,15073-15084. 

Wienk, M.M., Turbiez, M., Gilot, J., Janseen, R.A.J. Narrow-bandgap diketo-pyrrolo-pyrrole polymer solar cells the effect of processing on the performance. Adv. Mater. 20, 2556-2560 (2008)... 

It should be noted that a number of SPC polymers which contain other heterocycles have been prepared, motivated by their promising optical or electrical properties. Examples include pyridine (65) [123], pyrrole (66) [124], oxadiazole (67) [125], selenophene (68) [126], benzo[2,l,3]thiadiazole (69) [127], benzo[2,l,3]selenadiazole (70) [126], perylene bisimide (71) [128], 1,4-diketo- pyrrolo[3,4-c]pyrrole-l,4-dione (72 and 73) [127,129], and triphenyleamine (74) [127] as part of the polymer backbone by SPC (Figure 19c). Specifically for metal complexation, porphyrin [130], difluoroboraindacene [131], bipyridine [132], phenanthroHne [113], terpyridine [133, 134], and the like [123] were embedded in the backbone. In this context, an interesting report was submitted by Rehahn et al., in which l,l -ferrocenyl units were incorporated into a PPP (Figure 22.20). Due to a low-energy barrier for rotation around the Cp-Fe-Cp axes (Cp = cyclopentadienyl), the obtained polymer 75 was assumed to take randomly coiled conformations [135]. 

The sulfo derivatives (10) are used as dispersants for diketopyrrolopyrrole pigments in coatings and plastics. They are manufactured by chlorosulfonation of the diketop)m olopyrrole and subsequent condensation with the appropriate amine. For example, l,4-diketo-3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole was reacted with chlorosulfonic acid and thionyl chloride to give the sulfonyl chloride which was condensed with 3-(dimethylamino)-l-propylamine to yield the product. The dispersant was used with Cl Pigment Red 264 in the production of a coating (Chapter 8, Section 5). 

The photoconductivity of l,4-dithioketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole( XXV) was first reported by Mizuguchi and Rochat in 1988 [262]. It was synthesized from the corresponding diketo precursor with Lawesson s reagent. The crude product apparently is very impure and an extensive purification procedure was given, e.g., wash the crude pigment 3-4 times with solvents and then sublime 4 times under an argon atmosphere. 

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