Anthradithiophene (ADT), a thienoacene composed of five fused aromatic rings, is a promising building block for realizing π-conjugated systems for organic electronics, but its use remains rare because of its limited synthetic accessibility. We report here an innovative double annulation protocol combining, in one pot, a direct arylation and cross aldol condensation, for the regiospecific construction of π-extended angularly fused ADT-based scaffolds. The multi-gram scale synthetic protocol does not require lengthy chromatographic purifications, leading to very low values for E factors, warranting scalability and sustainability of the overall process. The ADT-based compounds can be efficiently derivatized on the α-positions of the fused thiophene residues. Two types of π-extended small molecules could be synthesized and characterized. Devices built with the p-type small molecule showed good hole mobilities independently from the applied field.

Anthradithiophene-based organic semiconductors through regiodirected double annulations

Nitti A.;Forti G.;Pasini D.
2021

Abstract

Anthradithiophene (ADT), a thienoacene composed of five fused aromatic rings, is a promising building block for realizing π-conjugated systems for organic electronics, but its use remains rare because of its limited synthetic accessibility. We report here an innovative double annulation protocol combining, in one pot, a direct arylation and cross aldol condensation, for the regiospecific construction of π-extended angularly fused ADT-based scaffolds. The multi-gram scale synthetic protocol does not require lengthy chromatographic purifications, leading to very low values for E factors, warranting scalability and sustainability of the overall process. The ADT-based compounds can be efficiently derivatized on the α-positions of the fused thiophene residues. Two types of π-extended small molecules could be synthesized and characterized. Devices built with the p-type small molecule showed good hole mobilities independently from the applied field.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11571/1438958
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 7
social impact