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The development of new organic semiconductors with improved electrical performance and enhanced environmental stability is the focus of considerable research activity. This paper presents the design, synthesis, optical and electrochemical characterization, crystal packing, modeling and thin film morphology, and organic thin film field effect transistor (OTFT) device data analysis for a novel 2,6-bis[2-(4-pentylphenyl)vinyl]anthracene (DPPVAnt) organic semiconductor. We observed a hole mobility of up to 1.28 cm2/V.s and on/off current ratios greater than 107 for OTFTs fabricated using DPPVAnt as an active semiconductor layer. The mobility value is comparable to that of the current best p-type semiconductor pentacene-based device performance. In addition, we found a very interesting relationship between the charge mobility and molecule crystal packing in addition to the thin film orientation and morphology of the semiconductor as determined from single-crystal molecule packing study, thin film X-ray diffraction, and AFM measurements. The high performance of the semiconductor ranks among the best performing p-type organic semiconductors reported so far and will be a very good candidate for applications in organic electronic devices.