Synthesis and C–H Functionalization Chemistry of Thiazole-Semicoronenediimides (TsCDIs) and -Coronenediimides (TCDIs)

Qinqin Shi, Eric S. Andreansky, Seth R. Marder, and Simon B. Blakey

J. Org. Chem.,
2017, 82, (19), 10139-10148; DOI:10.1021/acs.joc.7b01604


This collaborative report, that brings together two teams of CCHF researchers from Emory University and Georgia Institute of Technology, describes a novel, efficient and environmentally friendly approach to making materials capable of effective transport of electrons. These are critical components in materials used to harvest energy from the sun and cutting-edge flexible display screens.

Thiazolesemicoronenediimides (TsCDI’s) and coronenediimides (TCDI’s) are proven and effective building blocks for such materials, their specific electronic structures making them efficient in conducting electrons. However, conventional methods of creating these building blocks include methods that produce significant levels of harmful and environmentally damaging waste.

This report describes a direct C–H activation method that can be used to construct dimeric, trimeric and polymeric materials based on these building blocks in an efficient and environmentally friendly fashion.

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