Development of Indigo Derivatives as Functional Molecules with Novel Photochemical Properties

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During the first year, we completed the optimization of indigo mono-N-arylation. By using copper catalyst and inexpensive reagents, we were able to achieve selective and efficient transformation under mild reaction conditions. The examination of substrate scope revealed that various useful functional groups can be included, which is crucial for future applications of indigos in multiple scientific fields. With these compounds in hand, we built a series of photoswitches and studied their photochemical properties under red-light irradiation. In particular, by using data science approaches, the thermal stabilities were correlated with structural descriptors obtained by computations, which serves as a useful tool for predicting the properties of novel compounds. On the other hand, in an international collaborative project, we successfully identified the key parameters for red-light-enabled photoswitching of indigos in polymer thin films. This study is critical in understanding their different behaviors between solution and solid-state environment. Overall, these works have moved forward the understanding and utility of indigos as functional molecules and laid the important foundation for future studies.