Organic semiconductors have attracted interest for electronic applications due to their potential for use in low-cost, large-area, flexible electronic devices. Organic moieties with high electron affinity (EA) may act as intra- and intermolecular acceptors in pi-conjugated materials for applications in non-linear optics, organic light emitting diodes, organic photovoltaics, and organic field-effect transistors. However, incorporation of strong p-acceptors into either small molecule and polymer materials can be problematic since many high-EA precursors are resistant to electrophilic halogenation and lithiated derivatives typically used to form Stille and Suzuki reagents are often unstable. Direct C-H bond functionalization on sp<sup>2</sup> carbon centers has become a useful tool for the synthesis of pi-conjugated small molecules and polymers. Direct C-H arylation can be particularly useful in the synthesis of materials with high EA, where it may be used to circumvent some of the synthetic difficulties associated with strongly electron-accepting intermediates and with conventional cross-coupling partners. Electron acceptor and transport materials for organic photovoltaics and transistors synthesized by these direct C-H arylation methods will be discussed. The generally high yields of cross-coupling to high EA building blocks described herein help demonstrate that C-H arylation has potential to turn synthetic limitations associated with high EA substrates into a synthetic strength.

Design and synthesis of organic semiconductor

251st National Meeting (2016)

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