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2,6-Di(thiophenyl)-1,5-dihydrodipyrrolopyrazine (DT-DPP) structural isomers as donor–acceptor–donor molecules and their optoelectronic investigation

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Herein we report the synthesis and characterization of two new D–A–D molecules 1,5-dimethyl-2,6-di(thiophen-2-yl)-1,5-dihyrodipyrrolo[3,2-b:3′,2′-e]pyrazine (2DT-DPP) and 1,5-dimethyl-2,6-di(thiophen-3-yl)-1,5-dihyrodipyrrolo[3,2-b:3′,2′-e]pyrazine (3DT-DPP) via Pd catalyzed C–C and C–N coupling reactions. The dipyrrolopyrazine scaffold comprises an… Click to show full abstract

Herein we report the synthesis and characterization of two new D–A–D molecules 1,5-dimethyl-2,6-di(thiophen-2-yl)-1,5-dihyrodipyrrolo[3,2-b:3′,2′-e]pyrazine (2DT-DPP) and 1,5-dimethyl-2,6-di(thiophen-3-yl)-1,5-dihyrodipyrrolo[3,2-b:3′,2′-e]pyrazine (3DT-DPP) via Pd catalyzed C–C and C–N coupling reactions. The dipyrrolopyrazine scaffold comprises an electron-accepting core flanked by two thiophene moieties. To reveal the molecular geometry and molecular packing of 3DT-DPP, X-ray single crystal analysis was carried out. The surface morphological analysis shows the formation of microrods. The photophysical properties of these systems were characterized by UV-vis, fluorescence spectroscopy, and cyclic voltammetry. The thermal properties reveal that both the isomers are thermally stable up to 300 °C. This study clearly demonstrates that DT-DPP can be used to build D–A molecules to produce promising conjugated materials for various optoelectronic applications.

Keywords: dpp structural; structural isomers; dihydrodipyrrolopyrazine dpp; donor acceptor; isomers donor; thiophenyl dihydrodipyrrolopyrazine

Journal Title: RSC Advances
Year Published: 2017

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