Synthesis of organic building blocks featuring the ene-imine motif

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University of New Brunswick


Nitrogen-containing heterocycles, or building blocks, have been shown to possess outstanding properties, in small molecules and polymers, for applications in organic solar cells (OSCs), organic light-emitting diodes (OLEDs), and organic thin-film transistors (OTFTs). To further advance our understanding of structure-activity relationships in organic semiconductors, and to improve their performance, new organic building blocks that can be fine-tuned to have desired properties are required. The ene-imine conjugation pathway is of interest for various reasons. For example, boron-dipyrromethenes (BODIPYS) are planar, π-conjugated small molecules that can be tuned to absorb light in the red to near-infrared region, which is beneficial for applications such as organic electronics and bioimaging. However, available synthetic strategies toward BODIPY systems limits the scope of derivatives that can be achieved. Several ene-imine derivatives were prepared according to the developed synthetic procedure described herein in yields of 23-52% over two steps. The optical properties were determined by UV-vis, and the solid-state packing properties by X-ray crystallography.