The eight molecules (4, 5, 1-OMe, 2-OMe, 3-OMe, 5-OMe, 6-OMe, and 9-OMe) in Figure have computed λ max values that range from 367-415 nm and t 1/2 values that range from 5-290 days. Six of the eight photoswitches (4, 5, 2-OMe, 3-OMe, 4-OMe, and 5-OMe) are substituted with an EDG at the para position on the phenyl ring, which increased the λ max relative to an unsubstituted or EWGsubstituted Ph group. 1-OMe has the lowest λ max (367 nm) of the eight photoswitches in this quadrant. Six of the eight photoswitches in the green quadrant are substituted on the thiophene ring with methoxy groups, consistent with EDGs red-shifting the λ max of azoarene photoswitches. We also observed that extending 𝜋conjugation through a methoxy diene group significantly red-shifted the λ max of the photoswitches while maintaining a relatively longlived t 1/2 (as seen in 4, 5, and (4-5)-OMe). Our results show that all methoxy-substituted azothiophenes have lower ∆𝑮 ‡ than their corresponding analogs with unsubstituted thiophene rings (barriers decreased by 0.6 -3.5 kcal mol -1 ) while significantly increasing the λ max (24 -81 nm increase for the E-isomer). Due to the crossconjugation of the thiophene ring, the dimethoxy-substituted photoswitches offer red-shifted λ max and longer t 1/2 over previously reported azothiophenes.