4.6 Article

Aggregation Modes of Chiral Diketopyrrolo[3,4-c]pyrrole Dyes in Solution and Thin Films

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 51, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202201178

关键词

aggregation modes; diketopyrrolo[3; 4-c]pyrroles; electronic circular dichroism; supramolecular chirality; thin films

资金

  1. MIUR, Ministero dell' Istruzione, dellUniversita e della Ricerca (PRIN 2017 project CHIRALAB) [20172M3K5N]
  2. Universita di Pisa [PRA 2020_21]
  3. Universita degli Studi di Pisa within the CRUI-CARE Agreement

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This study investigates the chiroptical features of chiral DPP derivatives and reveals the superior capability of ECD spectroscopy compared to absorbance spectroscopy in detecting aggregation modes and multiple pathways.
The chiroptical features of chiral diketopyrrolo[3,4-c]pyrrole (DPP) derivatives have been only marginally investigated to date. In this regard, we have synthesized ad hoc four chiral DPP dyes, functionalized with enantiopure alkyl groups from natural sources either on the lactam moieties or on the terminal positions of the pi-conjugated backbone, to promote an efficient self-assembly into chiral supramolecular structures. For each of them, the aggregation modes has been investigated by absorbance and ECD spectroscopies in conditions of solution aggregation and on thin films, considering the effects of deposition technique (drop casting vs. spin coating) and post-deposition operations (solvent and thermal annealing). The effect of the structure of lateral pi-conjugated units attached to the central DPP scaffold, as well as that of the position of the alkyl chiral group, has been assessed. ECD revealed superior capability, compared to absorbance spectroscopy, to provide information on the aggregation modes and to detect the possible co-existence of multiple aggregation pathways.

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