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Eight stacked dimer arrangements were found, six of which are driven by the minimisation of electron repulsion and realised by placing the partially negatively charged atoms of the diketopyrrolopyrrole rings below the centre of an adjacent thiophene ring. Four of these stacks are related to <jats:italic>N<\/jats:italic>,<jats:italic>N'<\/jats:italic>\u2010dialkylated derivatives of ThDPP found in the literature, while a further one is related to an <jats:italic>N<\/jats:italic>,<jats:italic>N'<\/jats:italic>\u2010diacylated derivative. An analogous set of eight stacks was discovered computationally for phenyl\u2010substituted DPP (PhDPP), four of which are known among H\u2010bonded DPP pigments, and one more among <jats:italic>N<\/jats:italic>,<jats:italic>N'<\/jats:italic>\u2010dialkylated PhDPP derivatives. The results shed more light on the mechanisms that drive the formation of stacks between nonaromatic (DPP) and aromatic (Th, Ph) rings. 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