Carbamate-Functionalized N-Acetyl-D-Glucosamine Derivatives for Gel Formation and Chemiluminescent Properties of their Metallogels

Abstract Sugar-based low-molecular-weight gelators are an interesting and useful class of compounds due to their many applications. Several carbamate derivatives of d-glucose and d-glucosamine have been previously reported as effective gelators, demonstrating that the fine-tuning of molecular structures can have a profound influence on molecular assembling properties. In this study, a series of 12 3-O-carbamate derivatives of N-acetyl-d-glucosamine were synthesized in short steps with several derivatives found to be organogelators. The derivatives were screened in 11 different solvents for their gelation properties. Among the series of synthesized compounds, ten derivatives showed gelation in at least one of the tested solvents. Selected gelators were characterized and then evaluated for their metallogel formation and metal ion sensing abilities. The most versatile gelator in the series is the cyclohexyl derivative, compound 7, which formed gels in several solvents including DMSO/water and ethanol/water mixtures, as well as in the presence of various metal ions. The hydrogels formed by compound 7 in DMSO/water mixtures can be used for dye removal. In addition, the metallogels formed by the gelator demonstrated enhanced chemiluminescence for luminol and hydrogen peroxide.