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Article

Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties

by
Antonio Carella
1,*,
Alessandro Landi
2,
Matteo Bonomo
3,4,
Fabio Chiarella
5,
Roberto Centore
1,
Andrea Peluso
2,
Stefano Nejrotti
3,4 and
Mario Barra
5
1
Dipartimento di Scienze Chimiche, Università degli Studi di Napoli ‘Federico II’, Complesso Universitario Monte Sant’Angelo, Via Cintia 21, 80126 Napoli, Italy
2
Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
3
Department of Chemistry, University of Torino, Via Pietro Giuria 7, 10125 Torino, Italy
4
Nanomaterials for Industry and Sustainability (NIS) Interdepartmental Centre, Via G. Quarello 15A, 10135 Torino, Italy
5
CNR-Institute for Superconductors, Innovative Materials, and Devices, Dipartimento di Fisica “Ettore Pancini”, P. le Tecchio, 80, 80125 Napoli, Italy
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(12), 2805; https://doi.org/10.3390/molecules29122805
Submission received: 19 May 2024 / Revised: 6 June 2024 / Accepted: 10 June 2024 / Published: 12 June 2024
(This article belongs to the Section Materials Chemistry)
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Abstract

The diketopyrrolopyrrole (DPP) unit represents one of the building blocks more widely employed in the field of organic electronics; in most of the reported DPP-based small molecules, this unit represents the electron acceptor core symmetrically coupled to donor moieties, and the solubility is guaranteed by functionalizing lactamic nitrogens with long and branched alkyl tails. In this paper, we explored the possibility of modulating the solubility by realizing asymmetric DPP derivatives, where the molecular structure is extended in just one direction. Four novel derivatives have been prepared, characterized by a common dithyenil-DPP fragment and functionalized on one side by a thiophene unit linked to different auxiliary electron acceptor groups. As compared to previously reported symmetric analogs, the novel dyes showed an increased solubility in chloroform and proved to be soluble in THF as well. The novel dyes underwent a thorough optical and electrochemical characterization. Electronic properties were studied at the DFT levels. All the dyes were used as active layers in organic field effect transistors, showing balanced charge transport properties.
Keywords: diketopyrrolopyrrole; organic semiconductors; DFT; organic transistors; electrochemistry diketopyrrolopyrrole; organic semiconductors; DFT; organic transistors; electrochemistry

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MDPI and ACS Style

Carella, A.; Landi, A.; Bonomo, M.; Chiarella, F.; Centore, R.; Peluso, A.; Nejrotti, S.; Barra, M. Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties. Molecules 2024, 29, 2805. https://doi.org/10.3390/molecules29122805

AMA Style

Carella A, Landi A, Bonomo M, Chiarella F, Centore R, Peluso A, Nejrotti S, Barra M. Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties. Molecules. 2024; 29(12):2805. https://doi.org/10.3390/molecules29122805

Chicago/Turabian Style

Carella, Antonio, Alessandro Landi, Matteo Bonomo, Fabio Chiarella, Roberto Centore, Andrea Peluso, Stefano Nejrotti, and Mario Barra. 2024. "Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties" Molecules 29, no. 12: 2805. https://doi.org/10.3390/molecules29122805

APA Style

Carella, A., Landi, A., Bonomo, M., Chiarella, F., Centore, R., Peluso, A., Nejrotti, S., & Barra, M. (2024). Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties. Molecules, 29(12), 2805. https://doi.org/10.3390/molecules29122805

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