Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Perfluorinated and Half-Fluorinated Rubrenes: Synthesis and Crystal Packing Arrangements

Perfluorinated and Half-Fluorinated Rubrenes: Synthesis and Crystal Packing Arrangements
Toshiyasu Suzuki, Youichi Sakamoto
Perfluororubrene (PF-RUB) has been synthesized by cycloaddition of perfluorinated 1,3-diphenylisobenzofuran and 1,4-diphenyl-2,3-didehydronaphthalene followed by reductive deoxygenation. This method was easily applied for the synthesis of half-fluorinated rubrene (F14-RUB). The electrochemical measurements and DFT calculations indicate that perfluorination strongly lowers the HOMO and LUMO energies. Recrystallization and sublimation of PF-RUB gave two different crystals with planar and twisted conformations, respectively. In both cases, perfluorination leads to the formation of short C–F and F–F contacts and completely disrupts face-to-face π interactions. Single crystals of F14-RUB were grown by sublimation, and twisted molecules display the two-dimensional π-stacking with a face-to-face distance of 3.54 Å.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01383

DOI: 10.1021/acs.joc.7b01383

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