Synthesis of antisymmetric derivatives of diketopyrrolopyrrole class pigments which are compatible in organic liquid and solid phases and investigation of photophysical-photochemical behaviour in different matrices

In this study, the high performance class of diketopyrrolopyrrole (DPP) pigments which were antisymmetric on the 3 and 6 positions were synthesized and their solubility was examined to carry out N- and N,N?-alkylation processes.For this purpose, firstly 3,6-diphenyl DPP derivatives were synthesized and their N-alkylation reactions were carried out by changing the mole rates of the starting materials. Eventually, three N-alkyl derivatives were isolated.Secondly, the 7 DPP pigments which have different aromatic groups (phenyl, p-tolyl, p-methoxyphenyl and pyridine) on 3 and 6 positions were synthesized. Then, 3 different alkyl groups were connected to the nitrogen atoms of the DPP pigments and 13 soluble derivatives which known as N-alkyl and N,N?-dialkyl were obtained.All of the derivatives were characterized with FT-IR and 1H-NMR spectroscopic techniques. UV-vis absorption and emission spectra of the antisymmetric N-alkyl and N,N?-dialkyl derivatives were measured and their photophysical parameters and photostability behaviours were determined.Keywords: diketopyrrolopyrrole, dyes and pigments, absorption and emission, high performance pigments, optic sensor.