Bhunia Supriya, Dolai Anirban, Bera Satyajit, Samanta Subhas
Department of Chemistry, University of Calcutta, 92 Acharya Prafulla Chandra Road, Kolkata 700009, West Bengal, India.
J Org Chem. 2022 Mar 18;87(6):4449-4454. doi: 10.1021/acs.joc.1c02898. Epub 2022 Feb 24.
-Dimethylamine- and -pyrrolidine-substituted arylazopyrazoles display very high to near-quantitative or quantitative bidirectional isomerization under violet and green or red lights in both polar (DMSO and DMSO/aqueous buffer, pH 7.5) and nonpolar solvents. These switches confer a reasonable thermal stability to their -states ( ≈ 4-7 h in DMSO and DMSO/buffer) and also show a high level of resistance to photobleaching and an impressive stability to reduction by glutathione. Using DFT calculations, attempts have been made to decipher the photophysical properties and thermal stabilities of the cis isomers.
二甲基胺和吡咯烷取代的芳基偶氮吡唑在极性溶剂(二甲基亚砜和二甲基亚砜/水性缓冲液,pH 7.5)和非极性溶剂中,在紫光和绿光或红光下表现出非常高至接近定量或定量的双向异构化。这些开关赋予其状态合理的热稳定性(在二甲基亚砜和二甲基亚砜/缓冲液中约为4 - 7小时),还表现出对光漂白的高抗性以及对谷胱甘肽还原的显著稳定性。通过密度泛函理论计算,已尝试解读顺式异构体的光物理性质和热稳定性。