1206604-99-0Relevant academic research and scientific papers
New 3,4,5-trisubstituted isoxazole derivatives with potential biological properties
Bustos, Carlos,Molins, Elies,Cárcamo, Juan-Guillermo,Aguilar, Marcelo N.,Sánchez, Christian,Moreno-Villoslada, Ignacio,Nishide, Hiroyuki,Mesías-Salazar, Angela,Zarate, Ximena,Schott, Eduardo
, p. 4295 - 4307 (2015)
Synthesis of (E)-3,5-dimethyl-4-(R-phenyldiazenyl)isoxazoles was carried out by reacting β-diketohydrazones (R-C6H4-NHNC(COCH3)2) with hydroxylammonium chloride, where R = 4-N(CH3)2(1), 4-O
Acid-catalysed liquid-to-solid transitioning of arylazoisoxazole photoswitches
Arndt, Niklas B.,B?ckmann, Marcus,Doltsinis, Nikos L.,Kortekaas, Luuk,Ravoo, Bart Jan,Simke, Julian
, p. 11338 - 11346 (2021)
Molecular photoswitches play a vital role in the development of responsive materials. These molecular building blocks are particularly attractive when multiple stimuli can be combined to bring about physical changes, sometimes leading to unexpected properties and functions. The arylazoisoxazole molecular switch was recently shown to be capable of efficient photoreversible solid-to-liquid phase transitions with application in photoswitchable surface adhesion. Here, we show that the arylazoisoxazole forms thermally stable and photoisomerisable protonatedZ- andE-isomers in an apolar aprotic solvent when the pKaof the applied acid is sufficiently low. The tuning of isomerisation kinetics from days to seconds by the pKaof the acid not only opens up new reactivity in solution, but also the solid-state photoswitching of azoisoxazoles can be efficiently reversed with selected acid vapours, enabling acid-gated photoswitchable surface adhesion.
Arylazo-3,5-dimethylisoxazoles: Azoheteroarene Photoswitches Exhibiting High Z-Isomer Stability, Solid-State Photochromism, and Reversible Light-Induced Phase Transition
Devi, Sudha,Kumar, Pravesh,Sah, Chitranjan,Srivastava, Anjali,Venkataramani, Sugumar
, (2019/08/21)
Reversibly photoswitchable phenylazo-3,5-dimethylisoxazole and 37 aryl-substituted derivatives were synthesized. Excellent photoswitching ability of these compounds in solution and the solid state was demonstrated. Through kinetics studies by means of NMR spectroscopy, high Z-isomer stability was demonstrated. Interestingly, the majority of the derivatives showed light-induced contrasting color changes in solution and the solid state. Besides, many of the derivatives exhibit partial phase transition upon UV irradiation. The highlight of this class of photoswitches is the reversible light-induced phase transition between solid and liquid phases in the parent compound, which can be used in patterned crystallization. These results show that this new class of azoheteroarene based photoswitches has opportunities to be useful in various domains.
