In the field of p-conjugated nanohoops, the size of the macrocycle has a huge impact on its structural characteristics, which in turn affect its electronic properties. In this work, we report the first experimental investigations linking the size of a nanohoop to its charge transport properties, a key property in organic electronics. We describe the synthesis and the study of the first example of cyclocarbazole possessing five constituting building units, namely [5]-cyclo-N-butyl-2,7-carbazole [5]C-Bu-Cbz. By comparison with a shorter analogue, [4]-cyclo-N-butyl-2,7-carbazole [4]C-Bu-Cbz, we detail the photophysical, electrochemical, morphological and charge transport properties, highlighting the key role played by the hoop size. Particularly, we show that the saturated field effect mobility of [5]C-Bu-Cbz is four times higher than that of its smaller analogue [4]C-Bu-Cbz (4.22 × 10-5vs 1.04 × 10-5 cm².V-1.s-1). However, the study of the other OFET characteristics (threshold voltage VTH and subthreshold slope SS) suggest that a small nanohoop is beneficial for a good organization of the molecules in thin films whereas a large one increases the density of structural defects, and hence of traps for the charge carriers. The present findings are of interest for the further development of nanohoops in electronics.