Chiral Diketopyrrolo[3,4‐c]pyrrole‐1,2,3‐1H‐triazole Dyes with Highly Tuneable Properties in Solution and Thin Films

Abstract

We studied the impact of achiral substituents on the chiral supramolecular architectures of diketopyrrolo [3,4-c]pyrrole-1,2,3-1H-triazole (DPP) dyes. The same chiral DPP motif was decorated with three different achiral substituents on the nitrogen atoms of the lactam moiety: the hydrophobic n-octyl alkyl chain, the hydrophilic tri(ethylene glycol) (TEG) chain and the thermocleavable tert-butoxycarbonyl (tBoc) carbamate group. In spite of identical p-conjugated chromophore and chiral appendage, in aggregated form these three purple dyes displayed profoundly different optical, chiroptical, electrochemical and thermal features.