10.1016/j.tetlet.2014.01.056
The research presents a study on a selective fluorescence turn-on detection method for hydrogen peroxide (H2O2) and D-glucose, utilizing a tetraphenylethylene (TPE)-based molecule, compound 1. The detection mechanism relies on the aggregation-induced emission (AIE) behavior of the TPE unit and the reaction of H2O2 with the arylboronic ester group in compound 1. Upon reaction with H2O2, compound 1 transforms into compound 2, which is less soluble in water, leading to aggregation and a consequent fluorescence turn-on due to AIE properties. The study also demonstrates the application of compound 1 for the selective detection of D-glucose in aqueous solutions, leveraging the enzymatic oxidation of D-glucose by glucose oxidase (GOx) to produce H2O2, which then reacts with compound 1. The experiments involved the synthesis of compound 1, its characterization using 1H NMR, 13C NMR, and mass spectra, and fluorescence spectroscopy to monitor the reaction with H2O2 and the detection of D-glucose. The results showed high selectivity and sensitivity for H2O2 detection, with a low detection limit of 180 nM, and successful D-glucose detection down to a concentration of 3.0 μM. The selectivity was confirmed by testing the fluorescence response of compound 1 to other reactive oxygen species and sugars, with significant enhancement observed only in the presence of H2O2 and D-glucose.
10.1002/chem.201303522
The research focuses on the development of new aggregation-induced emission (AIE) active luminogens, specifically targeting the synthesis of efficient blue AIE emitters for undoped organic light-emitting diodes (OLEDs). The purpose of this study was to address the challenges associated with blue OLEDs, which often suffer from inferior performance due to the large band gap in blue luminogens. The researchers successfully synthesized two deep-blue fluorophores, TPE–pTPA and TPE–mTPA, along with six other compounds for comparison. These luminogens were designed to restrict the π-conjugation length, ensuring blue emission, by incorporating hole-dominated triphenylamine (TPA) and fluorene groups with high luminous efficiency, connected through unconjugated linkages. The study concluded that TPE–pTPA and TPE–mTPA exhibited the best electroluminescence performance with low turn-on voltages and high efficiencies, demonstrating that it is possible to enhance the OLED performance without sacrificing deep-blue emission through rational molecular design. Key chemicals used in the synthesis process included tetraphenylethene (TPE), triphenylamine (TPA), fluorene, and various other aromatic compounds. The researchers also utilized palladium-catalyzed Suzuki coupling reactions for the final product formation, with yields ranging from 60.4 to 85.9%. The compounds were purified and characterized using column chromatography and spectroscopic techniques.
10.1002/chem.201402152
The research aims to design and synthesize a highly efficient blue-emitting molecule with aggregation-induced emission (AIE) characteristics for organic light-emitting diodes (OLEDs). The study introduces a multifunctional AIE-active molecule, CzPySiTPE, which incorporates carbazole (Cz) and pyridine (Py) groups attached to a tetraphenylsilane core to facilitate carrier injection, while tetraphenylethene (TPE) is used to maintain efficient blue emission. The purpose is to enhance the performance of TPE-based OLEDs without sacrificing blue emission, addressing the challenge of developing efficient blue emitters. The results show that CzPySiTPE exhibits typical AIE properties, high thermal stability, and appropriate energy levels, achieving blue electroluminescence with CIE coordinates of (0.16, 0.17) and an external quantum efficiency of 1.12%. The study concludes that the incorporation of carbazole and pyridine groups enhances charge injection and carrier transport, leading to improved device efficiency, and demonstrates a new method for designing efficient solid-state bipolar blue materials.
10.1016/0040-4020(67)80009-7
The study investigates the carbenoid reaction of various compounds with alkyllithium in the presence of olefins. Dibromodiphenylmethane reacts with methyllithium in the presence of ethyl vinyl ether to produce 1,1-diphenyl-2-ethoxycyclopropane and tetraphenylethylene. However, 9,9-dibromofluorene and 9,9-dichloro-9H-tribenzo[a.c.e]cycloheptene do not yield cyclopropane derivatives under similar conditions but instead produce compounds like 9,9'-bifluorenylidene and 9-methylene-9H-tribenzo[a.c.e]cycloheptene. The study explores the mechanisms behind these reactions, suggesting that the formation of cyclopropane derivatives is influenced by the stability of intermediates and the steric hindrance around the reaction centers. The results indicate that the reactivity of these compounds with olefins cannot be fully explained by existing hypotheses and may involve different transition states and intermediates.
10.1002/asia.201100141
The study investigates the development of a fluorescence sensor for cholera toxin (CT) using tetraphenylethylene (TPE)-based glycoconjugates. The researchers synthesized TPE derivatives bearing lactosyl (Lac-TPE) and cellobiose (Cel-TPE) moieties through copper(I)-catalyzed "click reactions." Lac-TPE, due to its aggregation-induced emission (AIE) characteristics, exhibited a significant increase in fluorescence upon interaction with the cholera toxin B subunit (CTB), making it a potential sensor for CT detection. In contrast, Cel-TPE did not show any response to the toxin, highlighting the specificity of the interaction. The study demonstrates that the multivalent interactions between Lac-TPE and CTB enhance the binding affinity and specificity, leading to a "turn-on" fluorescence signal. This work provides a promising platform for detecting cholera toxin and investigating carbohydrate–protein interactions.