Synthesis and specific features of mesomorphic behavior of new polysubstituted triphenylenes

Abstract

Previously unknown 2,3,6,7,10,11 hexakis(dodecyloxy)triphenylene and (tetradecyl oxy)triphenylene were synthesized. The structures of the synthesized compounds were proved by elemental analysis and spectral methods. Polymesomorphism was found for the first time and studied for substances of the hexaalkoxytriphenylene homologic series, as well as liotropic mesomorphism in a series of organic solvents.

Molecular Triangles: Synthesis, Self‐Assembly, and Blue Emission of Cyclo‐7,10‐tris‐triphenylenyl Macrocycles

“…Hence, for the monomeric TP containing an identical number of six dodecyloxy chains, the transition to Col h occurred at a much lower temperature of 55 8C and the clearing point was reached at 63 8C. [11] The significantly stronger aggregation of macrocycle 9 is not only evidenced by higher phase transition temperatures, but also by the fact that heating the compound to temperatures of 400-450 8C does not lead to isotropization of the sample and is ultimately limited by the thermal decomposition of the macrocycle. A comparably broad liquid-crystalline phase width has also been reported for a related cyclo-3,6-trisphenanthrenyl macrocycle.…”

“…Monomeric, alkyl-substituted TPs have also been widely studied in the field of discotic liquid crystals owing to the formation of mesophases that are generally characterized by a high degree of organization. [6,7,[9][10][11] This structural perfection arises from the highly symmetric, disc-like aromatic core of TPs, which readily promotes their liquid crystallinity when decorated with peripheric alkyl chains. We were interested in the thermotropic behavior and the long-range selfassembly of the macrocyclic homologue 9, which preserved several important features of TP-based liquid crystals.…”

“…Cooling the sample to 30 8C, this halo remained unaffected, while the columnar arrangement changed to a rectangular unit cell with a rt = 2.96 nm and b rt = 2.03 nm. When the temperatures of the phase transitions are compared to the thermotropic data of 2,3,6,7,10,11-hexakis(dodecyloxy)triphenylene, [11] an increased intermolecular packing can be deduced for macrocycle 9. Hence, for the monomeric TP containing an identical number of six dodecyloxy chains, the transition to Col h occurred at a much lower temperature of 55 8C and the clearing point was reached at 63 8C.…”

“…[3,4] Monomeric TP derivatives received considerable interest when their liquid-crystalline nature was first reported, [5] spurring research in 2,3,6,7,10,11-hexasubstituted TP mesogens in particular. [6][7][8][9][10][11] Liquid crystallinity is driven by the strong p-stacking tendency of the planar TP core and van der Waals interactions of lateral side chains. Hexa-A C H T U N G T R E N N U N G alkoxytriphenylenes are of significant interest as fast photoconductors for applications in xerography.…”

Electrosynthesis and Characterization of 2, 3, 6, 7, 10, 11-Hexadecahexoxytriphenylene

“…Since 1,2-didecahexoxybenzene (DDHB) was not commercially available, high purity DDHB was synthesized using the well known Williamson method for preparation of ethers [13][14][15][16][17]. High purity cathecol (1,2-dihydroxybenzene) and 1-bromide-hexa-decane, were reduced using sodium in dry ethanol.…”