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Tuning of environmental probes

This thesis describes two projects focusing on (1) the investigation of benzoxadiazole chromophore and (2) new methods for solid phase microextraction. This thesis investigates how the diazole ring in nitrobenzoxadiazole affects environmental sensitivity. We developed a novel synthesis of isobenzofurans using anthranilic acid derivatives. The use of benzyne and bioorthogonal chemistry is used to achieve our isobenzofuran derivatives. This thesis will address two different ways in which to improve solid phase microextraction methods. By utilizing a novel cross linker and reverse addition fragmentation chain transfer (raft) polymerization we are able to control polymerization to give us more consistent polymers. We apply this method to creating dynamic polymers using a low critical solution temperature monomer. The other method utilizes our cross-link system to determine how film morphology affects the selectivity of poly ionic liquid polymers. This was done by investigating different percentages of cross linker. This project also led us to create a new cross-linker design containing another ionic liquid, allowing for further investigation into morphology. 1 CHAPTER 1. GENERAL INTRODUCTION This thesis will focus on two major topics, (1) the investigation into the environmental sensitivity of benzoxadiazole chromophores and (2) new material strategies for solidphase microextraction (SPME) methods. 1.1 Investigation into Benzoxadiazole Chromophores and Effects on Environmental Sensitivity So-called push-pull benzoxadiazoles (BD, Figure 1) are a class of environmentally sensitive dyes. These dyes have found applications in bioimaging to monitor interactions of proteins and lipids, among others.1,2 Since the creation of BD dyes, investigations have been made into how different electron donating (EDG) and electron donating groups (EWG) affect the environmental sensitivity of these dyes.3,4 Figure 1.1. Benzoxadiazole structure. To date, no studies have investigated what role the diazole ring might play. What effect do the nitrogen atoms in the diazole ring have on the environmental sensitivity—in polar-protic solvents in particular? In chapter two, I will discuss the synthesis of isobenzofuran with similar EDG and EWG of BD derivatives. With this structure we will investigate what effects the nitrogen atoms in the diazole ring have on environmental sensitivity. N O N EDG