Partial disorder is an inherent property of self-assembled organic semiconductors that complicates their rational design, because electronic structure, self-assembling properties, and stability all have to be accounted for simultaneously. Therefore, the understanding of charge transport mechanisms in these systems is still in its infancy. A theoretical study of charge transport in organic semiconductors was performed on self-assembled layers of [1]benzothieno[3,2-b]benzothiophene functionalized with alkyl side chains. Analysis showed that semiclassical dynamics misses static (on time scales of charge transport) disorder while the solution of the master equation combined with the high-temperature limit Marcus theory for charge transfer rates does not take into account molecular dynamic modes relaxing on a time scale of charge hopping. A comparison between predictions based on a perfectly ordered and a realistic crystal structure reveals the strong influence of static and dynamic disorder. The advantage of two-dimensional charge transporting materials over one-dimensional ones is clearly shown. The Marcus theory-based prediction of 0.1 cm 2 V -1 s -1 is in good agreement with our FET mobility of 0.22 cm 2 V -1 s -1, which is an order of magnitude lower than that reported in the literature [Ebata, H.; et al.
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