Multi-Potent Precursor Approach for the In-Situ Generation of Conjugated Polymers with Complementary Electronic Properties

Conjugated polymers, characterized by an extended π-conjugation along their backbone and a semiconductor behavior, have contributed dramatically to the rise of organic electronics, allowing the preparation of flexible and curved devices, cheap organic-based components, and wearable elements. Despite the immense capabilities of synthetic chemistry, however, there are still many materials that are elusive or not easily implemented because of their low processability. In some cases, the use of a polymeric precursor – designed to offer an improved solubility, processability, reactivity, or protection from environmental damage – provided a way to prepare and implement a material which was otherwise unprocessable or synthetically elusive, and which is obtained during the last step through a clean and high yielding transformation. While a precursor is usually designed to yield a unique compound, here we propose a novel approach in which a single precursor, based on substituted 9,10-dihydro-anthracene compounds, can be used to generate two different molecular structures characterized by complementary electronic properties (i.e. high-HOMO 9,10-diethynyl-anthracene units and low-LUMO anthraquinone units). Such transformations are achieved by different chemical treatments, which can also be applied orthogonally, thus generating different phases on a single substrate. We characterized the systems proposed and show several examples of how this methodology can be applied to the preparation of conjugated polymers and small molecules of interest in the field of organic electronics, redox polymers, electrochromic displays, and metal-ion organic batteries.