Aryl/fluoroaryl-substituted triphenylene discotic liquid crystals: Synthesis, mesomorphism, and photophysical properties

被引：0
|
作者：
He, Jiao [1 ]
Chen, Yang [1 ]
Hu, Ping [1 ]
Wang, Bi-Qin [1 ]
Zhao, Ke-Qing [1 ]
Donnio, Bertrand [2 ]
机构：
[1] College of Chemistry and Materials Science, Sichuan Normal University, Chengdu,610066, China
[2] Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), CNRS-Université de Strasbourg (UMR 7504), Cedex 2 Strasbourg, F-67034, France
来源：
Journal of Molecular Liquids | 2024年 / 414卷
关键词：
Fluorine aromatic hydrocarbons are ubiquitous optoelectronic functional materials and their efficient synthetic methods are still the subject of rapid, ongoing development. Here, several aryl- and fluoroaryl-substituted triphenylenes (Ar-TP/FAr-TP) were synthesized via either Suzuki-Miyaura cross-coupling or aromatic nucleophilic substitution (SNAr) of perfluoroarenes, respectively, starting indifferently from 2-bromo-3,6,7,10,11-pentakis(hexyloxy)triphenylene (Br-TP). These compounds possess very high thermal stability with initial decomposition temperature over 300 °C, as measured by thermal gravimetric analysis (TGA). Differential scanning calorimetry (DSC), polarized optical microscopy (POM), and small/wide angle X-ray scattering (S/WAXS) revealed that they all self-organize into hexagonal columnar (Colhex) mesophase over broad temperature ranges, occurring at room temperature for some of them, with higher stability than the archetypical 2,3,6,7,10,11-hexakis(hexyloxy)triphenylene parent compound. Under the combined influence of the conjugated π-system and core-side arm distortion, the clearing temperatures and mesophase ranges increase from phenyl- (P-TP), naphthyl- (N-TP), to biphenyl-triphenylene (BP-TP). The number of fluorine atoms on the side fluoroaryl group also impacts the columnar mesomorphism: the more fluorine atoms, the higher the clearing temperatures and the wider the Colhex phase ranges, concomitantly with increasing arene-fluorarene intermolecular interactions. In addition, these compounds show blue-violet photoluminescence in solution: the largest fluorescent absolute quantum yield is measured for BP-TP (45 %), while the smallest is for 7FN-TP (10 %). Perfluoroaryls tend to lower the LUMO, which results in fluorescence red-shift. The arene-perfluoroarene polar-π interactions improve the physical properties of these FAr-TP discotic liquid crystals. © 2024 The Author(s);
D O I：
10.1016/j.molliq.2024.126218
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