Synthesis and Self-Assembly of Liquid Crystalline Triphenylenedicarboxythioimides
- Resource Type
- Authors
- Katie M. Psutka; S. Holger Eichhorn; Hi Taing; Joshua LeDrew; Kenneth E. Maly
- Source
- The Journal of Organic Chemistry. 84:10796-10804
- Subject
- Crystallography
010405 organic chemistry
Chemistry
Liquid crystalline
Organic Chemistry
Mesophase
Self-assembly
010402 general chemistry
01 natural sciences
HOMO/LUMO
0104 chemical sciences
- Language
- ISSN
- 1520-6904
0022-3263
We report the synthesis and properties of a series of novel triphenylenedicarboxyimides and thioimides (4-6) 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.