Technologies that detect circularly polarized light (CPL), particularly in the UV region, have significant potential for various applications, including bioimaging and optical communication. However, a major challenge in directly sensing CPL arises from the conflicting requirements of planar structures for efficient charge transport and distorted structures for effective interaction with CPL. Here, a novel design of an axially chiral n‐type organic semiconductor is presented to surmount the challenge, in which a binaphthyl group results in a high dissymmetry factor at the molecular level, while maintaining excellent electron‐transporting characteristics through the naphthalene diimide group. Experimental and computational methods reveal different stacking behaviors in homochiral and heterochiral assemblies, yielding different structures: Nanowires and nanoparticles, respectively. Especially, the homochiral assemblies exhibit effective π–π stacking between naphthalene diimides despite axial chirality. Thus, phototransistors fabricated using enantiomers exhibit a high maximum electron mobility of 0.22 cm2 V−1 s−1 and a detectivity of 3.9 × 1012 Jones, alongside the CPL distinguishing ability with a dissymmetry factor of responsivity of 0.05. Furthermore, the material possesses a wide bandgap, contributing to its excellent visible‐blind UV‐selective detection. These findings highlight the new strategy for compact CPL detectors, coupled with the demonstration of less‐explored n‐type and UV region phototransistors.
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