Title

Developing a Basket-Shaped Host Molecule Based on P-Tert-Butylcalix[4]arene Featuring Urea Groups for Encapsulating Volatile Guest Molecules

Degree Name

Master of Science (MS)

Semester of Degree Completion

Summer 2019

Thesis Director

Zhiqing Yan

Thesis Committee Member

Rebecca A. Peebles

Thesis Committee Member

Robert W. Chestnut

Thesis Committee Member

Hongshan He

Abstract

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 a cavity for holding a much smaller guest molecule and tunable gates for keeping the guest molecule inside. These types of gates can be tuned by changing temperature, concentration, pH, etc. In this research group's previous study, a molecular basket of cal ix[ 4]arene with carboxylic acid groups was synthesized by functionalizing calix[4]arene's phenol hydroxyl groups with benzyl bromide building blocks. In the study detailed here, 1 , l '-((5-(bromomethyl)-1,3-phenylene)bis(methylene))bis(3-isopropylurea) was 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 that starts with 1,3,5-benzenetrimethanol. The synthetic intermediates were characterized by 1H, 13C NMR, and FT-IR spectroscopy analysis. The target host molecules were also characterized using mass spectrometry analysis.

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