Molecular baskets are a group of synthetic host molecules which are designed to govern the inclusion of small guest molecules. The basic structural features of basket-shaped host molecules are having a cavity to hold a much smaller guest molecule, as well as tunable gates to keep the guest molecule inside. These types of gates can be tuned by changing temperature, concentration, pH, etc. In our previous study, we synthesized a molecular basket of calix[4]arene with carboxylic acid groups by functionalizing calix[4]arene’s phenol hydroxyl groups with benzyl bromide building blocks. In our current study, 1,1'-((5-(bromomethyl)-1,3-phenylene)bis(methylene))bis(3-isopropylurea) will be assembled as the two gating arms for p-tert-butylcalix[4]arene. Synthesis of the urea featured benzyl bromide building block is a multistep process which starts with 1,3,5-benzenetrimethanol. The synthetic intermediates are characterized by 1H, 13C NMR and FT-IR spectroscopy analysis. The target host molecule will also be characterized using Mass spectrometry analysis. Benzaldehyde and its derivatives will be used as analogs of volatile guest molecules, which are expected to be encapsulated non-covalently inside the host molecule. The effects of external stimuli such as various temperatures upon the encapsulation will be studied.

Developing a basket-shaped host molecule based on calix[4]arene featuring urea groups for volatile guest molecules

2019 Spring National Meeting

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