A ligand-chirality controlled supramolecular hydrogel.
We report a novel example of ligand-chirality finely controlled in situ supramolecular hydrogel formation based on the coordination of phenylalanine (Phe) to Cu(II) with higher selectivity over other metal ions. As decreasing both enantiomeric excesses (ee%) of ligand Phe towards its D- and L-forms, the gelation ability of Phe-Cu(II) supramolecular metallogelator was found to be weakened and eventually disappeared, which likely resulted from the stereoselectivity of the ligand Phe. Intermolecular hydrogen bonding, hydrophobic and/or pi-pi stacking interactions were also found to be essential for forming the metallogel. We believe that the present work can open up a new entry for developing novel and promising chiral sensing and recognition platforms, i.e. visually sensing chiral molecules by naked eyes due to the feature of a sol-to-gel transition induced smartly by varying the ligand chirality.
Shen
Jiang-Shan
JS
Institute of Urban Environment, Chinese Academy of Sciences, Xiamen, 361021, China. jsshen@iue.ac.cn
Mao
Guo-Juan
GJ
Zhou
Yu-Hua
YH
Jiang
Yun-Bao
YB
Zhang
Hong-Wu
HW
D003198:Computer Simulation; D003300:Copper / Q000737:chemistry; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D046911:Macromolecular Substances / Q000138:chemical synthesis / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010316:Particle Size; D010649:Phenylalanine / Q000737:chemistry; D013499:Surface Properties
D008024:Ligands; D046911:Macromolecular Substances; D009942:Organometallic Compounds; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate; D010649:Phenylalanine; D003300:Copper