An organic semiconductor, expressed as a quadrupolar linear conjugated system (DPP Linear-c), consisting of a 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) central unit and two quaterfluorenylphenyl arms at the 3- and 6- positions of the DPP fragment, is studied in organic field effect transistors (OFETs). The strong propensity of DPP Linear-c to aggregate in the solid state favours the hole mobility of the semiconductor due to the alignment of HOMOs in the aggregates. The fabrication of OFETs from this novel p-type semiconductor is reported, using different dielectrics to evaluate their effect on the overall device performance. Despite its aggregation, DPP Linear-c remains luminescent in the solid state. Electroluminescence of a non-optimised OLED fabricated from this material is demonstrated.