title: Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors.
abstract: There is a great interest in peryleneimide (PI)-containing compounds given their unique combination of good electron accepting ability, high abosorption in the visible region, and outstanding chemical, thermal, and photochemical stabilities. Thus, herein we report the synthesis of perylene imide derivatives endowed with a 1,2-diketone functionality (PIDs) as efficient intermediates to easily access peryleneimide (PI)-containing organic semiconductors with enhanced absorption cross-section for the design of tunable semiconductor organic materials. Three processable organic molecular semiconductors containing thiophene and terthiophene moieties, PITa, PITb, and PITT, have been prepared from the novel PIDs. The tendency of these semiconductors for molecular aggregation have been investigated by NMR spectroscopy and supported by quantum chemical calculations. 2D NMR experiments and theoretical calculations point to an antiparallel π-stacking interaction as the most stable conformation in the aggregates. Investigation of the optical and electrochemical properties of the materials is also reported and analyzed in combination with DFT calculations. Although the derivatives presented here show modest electron mobilities of ∼10-4cm2V-1s-1, these preliminary studies of their performance in organic field effect transistors (OFETs) indicate the potential of these new building blocks as n-type semiconductors.
authors: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors: Paula
authors: P
authors: de Echegaray
authors: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors: María J
authors: MJ
authors: Mancheño
authors: Departamento de Química Física, Facultad de Ciencias, Universidad de Málaga , 29071 Málaga, Spain.
authors: Iratxe
authors: I
authors: Arrechea-Marcos
authors: Departamento de Tecnología Química y Ambiental, Universidad Rey Juan Carlos , Madrid 28933, Spain.
authors: Rafael
authors: R
authors: Juárez
authors: Departamento de Química Física, Facultad de Ciencias, Universidad de Málaga , 29071 Málaga, Spain.
authors: Guzmán
authors: G
authors: López-Espejo
authors: Departamento de Química Física, Facultad de Ciencias, Universidad de Málaga , 29071 Málaga, Spain.
authors: J Teodomiro
authors: JT
authors: López Navarrete
authors: Departamento de Tecnología Química y Ambiental, Universidad Rey Juan Carlos , Madrid 28933, Spain.
authors: María Mar
authors: MM
authors: Ramos
authors: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors: Carlos
authors: C
authors: Seoane
authors: Departamento de Química Física, Facultad de Ciencias, Universidad de Málaga , 29071 Málaga, Spain.
authors: Rocío Ponce
authors: RP
authors: Ortiz
authors: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors: José L
authors: JL
authors: Segura