Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: synthesis, photophysical and electrochemical properties, and self-assembly behavior

Abstract

We report the synthesis, photophysical properties, redox characteristics, and self-assembly behavior of disk-shaped trithiazolyl-1,3,5-triazines that bear decyloxybenzene moieties. These compounds were synthesized by a Migita-Kosugi-Stille coupling reaction of 1,3,5-trichlorotriazine with three different tributyltin(thiazoles) as the key step. The structure-property relationships, namely the effects of the incorporation of thiazole units into the triazine unit, the conjugation connectivity between the thiazole and triazine units, and the insertion of ethynylene spacers between the thiazole and decyloxybenzene moieties on the properties of the trithiazolyl-1,3,5-triazines were comprehensively investigated. Binding of the triazine core at the 5-position of the thiazole moieties effectively extended the π-conjugation and afforded high fluorescence quantum yields. The ethynylene spacers substantially lowered the LUMO level relative to the HOMO level. The prepared trithiazolyl-1,3,5-triazines self-assembled in solution, and the introduction of thiazole units at the 5-position enhanced this behavior. Detailed thermodynamic studies on the self-association behavior were conducted, and the formation of self-assembled 1D clusters is disclosed.

Experimental and DFT Study of the Photoluminescent Green Emission Band of Halogenated (−F, −Cl, and −Br) Imines

“…The experimental model applied in this paper has been reported in previous reports [25,43]. The correlation of the morphological properties associated with the optical response has motivated careful analysis of optical materials [44]. We chose of study in this region is because these materials generally absorb in the UV-region [45].…”

Composite Tetraheteroarylenes and Related Higher Cyclic Oligomers of Heteroarenes Produced by Palladium-Catalyzed Direct Coupling

“…Step 3] Synthesized according to the literature procedure. 24 A two-neck round-bottom flask equipped with an N2 balloon and a rubber cap was charged with 4-bromo-2phenylthiazole (717 mg, 3.0 mmol) and Et2O (20 mL). To a solution was added n-BuLi (1.6 mol/L in hexane, 3.6 mmol) dropwise at -78 °C, and the mixture was stirred at -50 °C for 30 min.…”

Self‐Assembly of Clicked Star‐Shaped Triazines into Functional Nanostructures

“…The TTT moiety can indeed be used as a core for H‐bonded supramolecular liquid crystals, leading to a modular approach to columnar mesophases that makes possible the design of ambipolar charge‐transporting materials . Some TTT and other similar triazine derivatives have shown attractive behaviors not only in the bulk, but also in solution, showing to be able to self‐aggregate in different solvents ,. This prompted us to investigate the self‐assembly of TTT‐based derivatives in the liquid phase, how to control the morphology of the aggregates and the consequences that the formation of the aggregates has on their optical properties.…”