Presentation Title

Efficient Synthesis of Novel Triazole Chemosensors Using Click-Chemistry

Location

Nessmith-Lane Atrium

Session Format

Poster Presentation

Research Area Topic:

Natural & Physical Sciences - Chemistry

Abstract

Cations and anions play essential roles in biological and physiological processes, however an imbalance in ion concentration whether an over- or under-supply of the wrong ion can be detrimental. For example, fluoride anions are often used in dentistry to prevent tooth decay, however excessive exposure can cause fluorosis. With children being the most susceptible, symptoms include bone damage and the brown mottling of teeth. The ability to detect and mobilize ions can be used to maintain an appropriate balance and prevent toxic effects. For detection purposes, scientists have employed the help of chemosensors. With these chemosensors the targeted analyte induces an optical or electrochemical response that allows scientists to identify, and in some cases, quantify and transport the ions. Hence chemosensors are utilized in various fields of science including medical imaging, cancer treatment, drug delivery, and environmental toxicology. In the case of most chemosensors the target analyte binds to the receptor that is covalently bonded to the signaling sub-unit and produces a reversible signal. Unfortunately, the seemingly simplistic approach of an analyte binding to a receptor is typically complicated with difficult and expensive synthetic procedures to create the receptors. However with the introduction of click chemistry by Sharpless, scientists are able to generate inexpensive chemosensors with less difficulty. Click chemistry describes a group of reactions that are simple to use, produce high yields of product, easy to purify, and react quickly. Of those click reactions the azide-alkyne cycloaddition meets all the requirements, while producing 1,2,3-triazoles. The 1,2,3,-triazoles are known to be effective in detecting both cations and anions, though the cation and anions that the triazole motif is able to detect is highly dependent on the substituents. The versatility of triazoles allows for an array of substituents to be added onto the motif, thus producing diverse optical signals. The utilizations of the motif are near limitless, with significant applications in environmental toxicology, medical imaging, anti-cancer, and anti-viral compounds. The goal of this study is to utilize click-chemistry to synthesize inexpensive triazole sensors capable of producing an on or off optical signal upon binding to the target cation or anion. A combination of analytical methods including NMR, IR, and mass spectrometry are used to elucidate the structure of our triazole sensors. Here in, results for the ongoing research into the syntheses of novel chemosensors and their precursors will be presented.

Presentation Type and Release Option

Presentation (Open Access)

Start Date

4-16-2016 10:45 AM

End Date

4-16-2016 12:00 PM

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Apr 16th, 10:45 AM Apr 16th, 12:00 PM

Efficient Synthesis of Novel Triazole Chemosensors Using Click-Chemistry

Nessmith-Lane Atrium

Cations and anions play essential roles in biological and physiological processes, however an imbalance in ion concentration whether an over- or under-supply of the wrong ion can be detrimental. For example, fluoride anions are often used in dentistry to prevent tooth decay, however excessive exposure can cause fluorosis. With children being the most susceptible, symptoms include bone damage and the brown mottling of teeth. The ability to detect and mobilize ions can be used to maintain an appropriate balance and prevent toxic effects. For detection purposes, scientists have employed the help of chemosensors. With these chemosensors the targeted analyte induces an optical or electrochemical response that allows scientists to identify, and in some cases, quantify and transport the ions. Hence chemosensors are utilized in various fields of science including medical imaging, cancer treatment, drug delivery, and environmental toxicology. In the case of most chemosensors the target analyte binds to the receptor that is covalently bonded to the signaling sub-unit and produces a reversible signal. Unfortunately, the seemingly simplistic approach of an analyte binding to a receptor is typically complicated with difficult and expensive synthetic procedures to create the receptors. However with the introduction of click chemistry by Sharpless, scientists are able to generate inexpensive chemosensors with less difficulty. Click chemistry describes a group of reactions that are simple to use, produce high yields of product, easy to purify, and react quickly. Of those click reactions the azide-alkyne cycloaddition meets all the requirements, while producing 1,2,3-triazoles. The 1,2,3,-triazoles are known to be effective in detecting both cations and anions, though the cation and anions that the triazole motif is able to detect is highly dependent on the substituents. The versatility of triazoles allows for an array of substituents to be added onto the motif, thus producing diverse optical signals. The utilizations of the motif are near limitless, with significant applications in environmental toxicology, medical imaging, anti-cancer, and anti-viral compounds. The goal of this study is to utilize click-chemistry to synthesize inexpensive triazole sensors capable of producing an on or off optical signal upon binding to the target cation or anion. A combination of analytical methods including NMR, IR, and mass spectrometry are used to elucidate the structure of our triazole sensors. Here in, results for the ongoing research into the syntheses of novel chemosensors and their precursors will be presented.