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Chiral diketopyrrolo[3,4‐c]pyrrole–1,2,3‐1H‐triazole dyes with highly tunable properties in solution and thin films

DOI: 10.1002/chem.202300291 DOI Help

Authors: Gianluigi Albano (Universita degli Studi di Bari) , Francesco Zinna (Università di Pisa) , Andrea Taddeucci (Università di Pisa; Diamond Light Source) , Maria Annunziata M. Capozzi (Università degli Studi di Bari Aldo Moro) , Gennaro Pescitelli (Università di Pisa) , Angela Punzi (Universita degli Studi di Bari Aldo Moro) , Lorenzo Di Bari (Università di Pisa) , Gianluca M. Farinola (Università degli Studi di Bari Aldo Moro)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry – A European Journal

State: Published (Approved)
Published: March 2023

Open Access Open Access

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. 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 triethylene glycol (TEG) chain and the thermo-cleavable t-butoxycarbonyl (t-Boc) carbamate group. In spite of identical conjugated chromophore and chiral appendage, 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.

Journal Keywords: chirality; diketopyrrolo[3,4-c]pyrroles; organic dyes; supramolecular chemistry; 1,2,3-1H-triazoles

Subject Areas: Chemistry, Physics

Technical Areas:

Added On: 28/03/2023 20:37

Chemistry A European J - 2023 - Albano - Chiral diketopyrrolo 3 4%E2%80%90c pyrrole 1 2 3%E2%80%901H%E2%80%90triazole dyes with highly tunable.pdf

Discipline Tags:

Surfaces Physics Physical Chemistry Electronics Chemistry interfaces and thin films Organic Chemistry

Technical Tags: