Graduate Program

Chemistry

Degree Name

Master of Science (MS)

Semester of Degree Completion

2019

Thesis Director

Zhiqing Yan

Thesis Committee Member

Rebecca A. Peebles

Thesis Committee Member

Hongshan He

Thesis Committee Member

Daniel J. Sheeran

Abstract

Nowadays molecular and supramolecular chemistry have endless examples for the development of smart devices. Among those applications, nano-baskets of calixarenes play vital roles in host-guest chemistry. One of the main appealing concepts of this field is the development of host molecules with gate features. These hosts are designed and constructed for the delivery of chemical or biochemical species that are volatile, or reactive, or sensitive to normal solution environment and they are mainly functioned by predefined groups that are responsive toward stimuli such as concentration, temperature, pH and so on. In our previous study, we found that benzyl bromides can be used to extend the phenol groups of p-tert-butylcalix[4]arene. In our original design of the current study, 5-(bromomethyl)-1,3-phenylene) diacetic acid will facilitate the formation of two extension arms for p-tert-butylcalix[4]arene. The extension arms are expected to act as a gate responding upon pH changes.

A precursor of the extension arm has been synthesized through multi-step process. Synthetic intermediates and the target molecules are characterized by 1H NMR, 13C NMR, FTIR and mass spectrometry analysis. The synthetic target molecule is expected to act as a host molecule, and benzaldehyde was investigated as potential guest molecule to mimic fragrance and/or volatile compounds. Gate features will be investigated by breaking and reforming of the in the intramolecular diacid assembly under the influence of pH changes of the media.

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