Abstract
Reversibly switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. This work presents a symmetrical benzothiadiazole (BTD) derivative with a high fluorescence quantum yield in solution and in the crystalline state and shows by spectroelectrochemical analysis that reversible switching of UV absorption in the neutral state, to broadband Vis/NIR absorption in the 1st oxidized state, to sharp band Vis absorption in the 2nd oxidized state, is possible. For the one‐electron oxidized species, formation of a delocalized radical is confirmed by electron paramagnetic resonance spectroelectrochemistry. Furthermore, our results reveal an increasing quinoidal distortion upon the 1st and 2nd oxidation, which can be used as the leitmotif for the development of BTD based redox switches.
Highlights
Switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics
We have recently demonstrated that switching the absorption between UV and Vis/NIR by redox processes seems to be feasible with small molecule BTD derivatives.[6]
We proved that the compound follows the Lambert–Beer law, even in EtOH, where it is least soluble by two dilution series, one in DCM and one in EtOH (Figure S20)
Summary
Switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. We have recently demonstrated that switching the absorption between UV and Vis/NIR by redox processes seems to be feasible with small molecule BTD derivatives.[6] These derivatives (Figure 1 A) lacked the desired reversibility of the redox processes.
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