Asymmetrical Diketopyrrolopyrrole Derivatives with Improved Solubility and Balanced Charge Transport Properties
Antonio Carella,
Alessandro Landi,
Matteo Bonomo,
Fabio Chiarella,
Roberto Centore,
Andrea Peluso,
Stefano Nejrotti,
Mario Barra
Affiliations
Antonio Carella
Dipartimento di Scienze Chimiche, Università degli Studi di Napoli ‘Federico II’, Complesso Universitario Monte Sant’Angelo, Via Cintia 21, 80126 Napoli, Italy
Alessandro Landi
Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Matteo Bonomo
Department of Chemistry, University of Torino, Via Pietro Giuria 7, 10125 Torino, Italy
Fabio Chiarella
CNR-Institute for Superconductors, Innovative Materials, and Devices, Dipartimento di Fisica “Ettore Pancini”, P. le Tecchio, 80, 80125 Napoli, Italy
Roberto Centore
Dipartimento di Scienze Chimiche, Università degli Studi di Napoli ‘Federico II’, Complesso Universitario Monte Sant’Angelo, Via Cintia 21, 80126 Napoli, Italy
Andrea Peluso
Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 84084 Fisciano, Italy
Stefano Nejrotti
Department of Chemistry, University of Torino, Via Pietro Giuria 7, 10125 Torino, Italy
Mario Barra
CNR-Institute for Superconductors, Innovative Materials, and Devices, Dipartimento di Fisica “Ettore Pancini”, P. le Tecchio, 80, 80125 Napoli, Italy
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.
