We report a new synthetic route to 5,11-disubstituted indeno[1,2-b]fluorene-6,12-diones that is amenable to larger scale reactions, allowing for the preparation of gram amounts of material. With this new methodology, we explored the effects on crystal packing morphology for the indeno[1,2-b]fluorene-6,12-diones by varying the substituents on the silylethynyl groups.
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We thank the National Science Foundation (CHE-1013032 & CHE-1301485) for support of this research. B.D.R. acknowledges the American Chemical Society Division of Organic Chemistry for an Emmanuil Troyanski Fellowship as well as the NSF for a GK-12 Fellowship (DGE-0742540). P.J.S.M. acknowledges the NSF for an REU Summer Fellowship (CHE-1062512).
Rose, Bradley D.; Santa Maria, Peter J.; Fix, Aaron G.; Vonnegut, Chris L.; Zakharov, Lev N.; Parkin, Sean R.; and Haley, Michael M., "Scalable Synthesis of 5,11-diethynylated Indeno[1,2-b]fluorene-6,12-diones and Exploration of Their Solid State Packing" (2014). Chemistry Faculty Publications. 36.