28084-35-7Relevant academic research and scientific papers
Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
Zhou, Yuntao,Piergentili, Irene,Hong, Jennifer,Helm, Michelle P. Van Der,MacChione, Mariano,Li, Yao,Eelkema, Rienk,Luo, Sanzhong
supporting information, p. 6035 - 6040 (2020/10/02)
Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional anilinecatalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.
Reversible photo-gated transmembrane channel assembled from an acylhydrazone-containing crown ether triad
Zhou, Yan,Chen, Yong,Zhu, Ping-Ping,Si, Wen,Hou, Jun-Li,Liu, Yu
supporting information, p. 3681 - 3684 (2017/04/03)
We have prepared a crown ether triad containing acylhydrazone units. In solution, the triad can self-assemble linearly to form an organogel. UV light-induced E/Z isomerization of the C=N bond of the acylhydrazone unit endows the assembly with photo-sensit
A toolbox for controlling the properties and functionalisation of hydrazone-based supramolecular hydrogels
Poolman, Jos M.,Maity, Chandan,Boekhoven, Job,Van Der Mee, Lars,Le Sage, Vincent A.A.,Groenewold, G.J. Mirjam,Van Kasteren, Sander I.,Versluis, Frank,Van Esch, Jan H.,Eelkema, Rienk
supporting information, p. 852 - 858 (2016/02/05)
In recent years, we have developed a low molecular weight hydrogelator system that is formed in situ under ambient conditions through catalysed hydrazone formation between two individually non-gelating components. In this contribution, we describe a molecular toolbox based on this system which allows us to (1) investigate the limits of gel formation and fine-tuning of their bulk properties, (2) introduce multicolour fluorescent probes in an easy fashion to enable high-resolution imaging, and (3) chemically modify the supramolecular gel fibres through click and non-covalent chemistry, to expand the functionality of the resultant materials. In this paper we show preliminary applications of this toolbox, enabling covalent and non-covalent functionalisation of the gel network with proteins and multicolour imaging of hydrogel networks with embedded mammalian cells and their substructures. Overall, the results show that the toolbox allows for on demand gel network visualisation and functionalisation, enabling a wealth of applications in the areas of chemical biology and smart materials.
