Small molecule-based organic semiconducting materials have applications in organic field effect transistors and organic photovoltaic devices. In light of the recent energy crisis, the study of organic photovoltaic devices has become an important research topic. A central aspect in this field is studying the relationship between molecular structure, crystal structure and electronic properties. Rubrene (5,6,11,12-tetraphenyltetracene) is a benchmark organic semiconductor. Its unique crystal packing is thought to give rise to its desirable electronic properties. Understanding and controlling the packing in rubrene derivatives is the focus of our work. The impact of electron-withdrawing and electron-donating functionality on the side phenyl groups was studied using a new modular, late-stage diversification synthetic approach. Several modifications to our synthesis were developed to install the desired functionality. The new derivatives were analyzed using X-ray crystallography to determine the packing structure. Analysis of the crystal structures has provided insight into the structural elements needed to prepare derivatives that retain the desirable packing motif observed in rubrene.

Synthesis and crystal structure engineering of rubrene derivatives for use in organic electronic devices

247th National Meeting (2014)

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