Crystal engineering [2+2] photodimerizations via templates and hydrogen bonds: Case of styrylthiophenes

© The Royal Society of Chemistry 2016. Crystal engineering strategies have been used to modify solid-state packings to direct [2+2] photodimerizations of olefinic compounds that are photostable as pure solids. The strategies have herein been expanded to achieve rare [2+2] photodimerizations of styrylthiophenes. Two co-crystallization approaches based on hydrogen-bond-driven self-assembly are employed to achieve the photodimerizations that yield regioisomers of a b-substituted thiophene. We expect the co-crystal strategies can be applied to modify solid-state packing as well as achieve photodimerizations of olefins substituted with other unique organic functional groups.