Concomitant crystallization of a hydrocarbon as conformational polymorphs

CHED 292

Rebecca I. Goldstein, Timothy R. Newhouse, tim.newhouse@gmail.com, Dasan M. Thamattoor, dmthamat@colby.edu, and Rebecca R. Conry, rrconry@colby.edu. Department of Chemistry, Colby College, 5750 Mayflower Hill, Waterville, ME 04901
Concomitant polymorphism refers to a process where two or more different forms (polymorphs) of a single compound crystallize out of the same solution. This is a rare occurrence as polymorphs typically form under different conditions, and thus concomitant polymorphism has been only reported for a small number of compounds. In our recent investigation into the photolysis of bis(9-anthryl)cyclopropenone (1) into bis(9-anthryl)acetylene, we serendipitously discovered that the product crystallizes as two distinct polymorphs from the same solution. One polymorph (2a), which is known, is essentially planar but in the other (2b) the two anthracene planes are twisted away from each other at an angle of about 67°. The synthesis, x-ray diffraction studies, and molecular orbital calculations of these polymorphic species are discussed.