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We have studied the impact of achiral substituents on the chiral supramolecular architectures of diketopyrrolo[3,4‐c]pyrrole‐1,2,3‐1H‐triazole (DPP) dyes. We decorated the same chiral DPP motif with substituent groups on the nitrogen atoms of the lactam moiety: the hydrophobic n‐octyl alkyl chain, the hydrophilic tri(ethylene glycol) (TEG) chain and the thermo‐cleavable tert‐butoxycarbonyl (t‐Boc) carbamate group. In spite of having identical conjugated chromophore and chiral appendages, in aggregated form the three dyes displayed profoundly different optical, chiroptical, electrochemical and thermal features. ECD measurements revealed differences in the aggregation modes, which would be inaccessible by most other techniques. We found strong chiroptical features, which would have major implications in the context of chiral organic opto‐electronics and in the development of other highly innovative technological applications. [ABSTRACT FROM AUTHOR]

Three diketopyrrolo[3,4- I c i ]pyrrole-1,2,3-1 I H i -triazole (DPP) dyes bearing the same chiral appendage R* but decorated with different achiral substituent groups Y showed profoundly different optical, chiroptical, electrochemical and thermal features in their aggregated form. Keywords: chirality; diketopyrrolopyrroles; organic dyes; supramolecular chemistry; triazoles EN chirality diketopyrrolopyrroles organic dyes supramolecular chemistry triazoles 1 1 1 06/21/23 20230619 NES 230619 B Supramolecular chirality b is far from being determined only by local stereogenic elements. Chirality, diketopyrrolopyrroles, organic dyes, supramolecular chemistry, triazoles. [Extracted from the article]