Brilaroxazine

High and increasing production of separation of C8 aromatic isomers demands the development of purification methods that are efficient, scalable, and inexpensive, especially for p-xylene, PX, the largest volume C8 commodity. Herein, we report that 4-(1H-1,2,4-triazol-1-yl)-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (TPBD), a molecular compound that can be prepared and scaled up via solid-state synthesis, exhibits exceptional PX selectivity over each of the other C8 isomers, o-xylene (OX), m-xylene (MX), and ethylbenzene (EB). The apohost or α form of TPBD was found to exhibit conformational polymorphism in the solid state enabled by rotation of its triazole and benzene rings. TPBD-αI and TPBD-αII are nonporous polymorphs that transformed to the same PX inclusion compound, TPBD-PX, upon contact with liquid PX. TPBD enabled highly selective capture of PX, as established by competitive slurry experiments involving various molar ratios in binary, ternary, and quaternary mixtures of C8 aromatics. Binary selectivity values for PX as determined by ¹H NMR spectroscopy and gas chromatography ranged from 22.4 to 108.4, setting new benchmarks for both PX/MX (70.3) and PX/EB (59.9) selectivity as well as close to benchmark selectivity for PX/OX (108.4). To our knowledge, TPBD is the first material of any class to exhibit such high across-the-board PX selectivity from quaternary mixtures of C8 aromatics under ambient conditions. Crystallographic and computational studies provide structural insight into the PX binding site in TPBD-PX, whereas thermal stability and capture kinetics were determined by variable-temperature powder X-ray diffraction and slurry tests, respectively. That TPBD offers benchmark PX selectivity and facile recyclability makes it a prototypal molecular compound for PX purification or capture under ambient conditions.

Luminol and its derivatives are extensively used as chemiluminogenic substrates in bioimaging and biochemical analysis. Luminol reagents can typically emit blue chemiluminescence (CL), whose wavelength is normally outside the most sensitive detection range of human naked eyes and most CL analyzers with silicon-based charge-coupled device (CCD) detectors. Development of luminol analogues with longer wavelength emission is thus attractive. Herein, four new phthalhydrazide CL probes (GL-1/2/3/4) have been prepared through the derivatization of luminol. The most promising one, 5-(4-hydroxy-1,3-dioxoisoindolin-2-yl)-2,3-dihydrophthalazine-1,4-dione (GL-1), emits bright green CL upon oxidation and shows enhanced CL performance compared to its parent luminol. Bloodstain imaging, horseradish peroxidase (HRP)-based immunoassay, and the analysis of glucose/glucose oxidase reaction have been performed using the GL-1 reagent. These results indicate that GL-1 is a new chemiluminogenic luminol analogue with great potential in real analytical applications and will be an alternative to replace luminol in practical CL analysis.