Anthradithiophene-based organic semiconductors through regiodirected double annulations. Issue 29 (6th July 2021)

• Record Type: Journal Article
• Authors: Nitti, Andrea; Forti, Giacomo; Bianchi, Gabriele; Botta, Chiara; Tinti, Francesca; Gazzano, Massimo; Camaioni, Nadia; Po, Riccardo; Pasini, Dario
• Is Part Of: Journal of materials chemistry. Volume 9:Issue 29(2021)
• Page Start: 9302
• Page End: 9308
• Publication Date: 2021-07-06
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/d1tc01887f
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : An innovative double annulation regiospecific synthesis of angularly fused anthradithiophene-based scaffolds is reported, carried out with very low values for E factors. Further functionalization affords small molecules as semiconducting organic materials. 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.