Psutka Katie M, LeDrew Joshua, Taing Hi, Eichhorn S Holger, Maly Kenneth E
Department of Chemistry & Biochemistry , Wilfrid Laurier University , Waterloo , Ontario N2L 3C5 , Canada.
Department of Chemistry & Biochemistry , University of Windsor , Windsor , Ontario N9B 3P4 , Canada.
J Org Chem. 2019 Sep 6;84(17):10796-10804. doi: 10.1021/acs.joc.9b01330. Epub 2019 Aug 13.
We report the synthesis and properties of a series of novel triphenylenedicarboxyimides and thioimides (-) to probe the effect of thionation on the formation of columnar mesophases. These materials display broad columnar mesophases and high clearing points and self-associate in solution to form dimers. Overall, thionation improved the self-assembly in solution and led to a stabilization of the columnar mesophase. Furthermore, increasing the thionation of these materials led to a lowering of the lowest unoccupied molecular orbital (LUMO) energy level and a narrowing of the highest occupied molecular orbital-LUMO gap.
