Small organic molecules with efficient emissions in both solid and solution state have applications in organic electronics and the field of fluorescent bioimaging. A common approach to access functional small molecules includes tethering together conjugated electron-rich and electron-poor moieties to create donor acceptor type motifs. Increased photoluminescent quantum yield, thermal stability, and redox characteristics can be achieved using the donor-acceptor design approach in small molecules. However, there still exist barriers related to the efficient synthesis of organic compounds with properties required to achieve the full commercial potential of these technologies. Herein is reported a one-step synthesis to access a series of donor-acceptor type diarylmaleimides (3a-h) with a range of photophysical and redox characteristics. Additionally, optical and electronic properties within the diarylmaleimides (3-8) were controllable through the strategic choice of the donor moiety (2a-h). This D-A system and approach provides a means to access and tailor properties for applications in organic electronics and fluorescent bioimaging, and allows structure-property relationships to be explored to further our design strategy.

Suzuki catalyzed one-step access to photoluminescent D-A type diarylmaleimides

2019 Fall National Meeting

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