1,2,3-Triazole–Diketopyrrolopyrrole Derivatives with TunableSolubility and Intermolecular Interactions

1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene–diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.This work was financially supported by the Ministero dell'Istruzi-one, dell'Università e della Ricerca (MIUR) [Progetto PRIN 2012prot. 2012A4Z2RY”, “Project PON02_00563_3316357 (PONMAAT), and Project PON03PE_00004_1 (PON MAIND)]. Thiswork was also supported by the Dirección General de Investiga-ción y Gestión del Plan Nacional de I+D+i (DGI) of the Ministeriode Ciencia y Tecnología (Spain) (Grant BE-WELL CTQ2013-40480-R), Agència de Gestió d'Ajuts Universitaris i de Recerca(AGAUR), Generalitat de Catalunya (Grant 2014-SGR-17), and theNetworking Research Center on Bioengineering, Biomaterials,and Nanomedicine (CIBER-BBN). D. B. and A. A. acknowledgethe European Commission (EC) FP7-PEOPLE-2013-Initial Train-ing Networks (ITN) (NANO2FUN Project No. 607721) for theirpredoctoral contracts.Peer reviewe