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We report an effective strategy for improving the electronic transport and switching behaviors of dimethyldihydropyrene/cyclophanediene (DHP/CPD)-based molecular devices, an intriguing photoswitch that can be triggered by ultraviolet/visible (UV-vis) light irradiation. Aiming to obtain molecular devices with high on-off ratios, we assess a series of molecular designs formed by [e]-fusing different arenes on a conjugated macrocycle to modulate the photochemical and electronic properties. Here, the switching mechanism and transport prope