Standing
Undergraduate
Type of Proposal
Oral Presentation
Faculty
Faculty of Science
Faculty Sponsor
Dr. John Trant
Proposal
Triggerable end-caps are a fascinating new tool in the field of material, environment and medicinal sciences that can be used for a variety of applications including the on-command degradation of self-immolative polymers. These end caps can be made sensitive to a diverse range of parameters including light, pH and enzymes. However, using heat might be of great utility for biomedical applications as it can be localized to a specific site through a number of non-invasive methods. The Trant group has prepared a number of heat-sensitive end-caps, and this study extends the scope and temperature range available to us by modifying the basic structure. These are synthesized through an efficient Diels-Alder reaction between a substituted furan and maleimide that allows for reversibility at a range of temperatures: the temperature at which the end-caps undergo retro-Diels-Alder reactions can be controlled through functionalization of these components. The role of furan functionalization with various electron donating and withdrawing groups was investigated, however steric effects played a significant role in the formation of the end-caps and it was difficult to determine the electronic effect on end-cap stability. To overcome this, furans with various para-substituted phenyls covering a range of electron withdrawing and donating groups were utilized where the steric effects are minimized, allowing the electronic effects to be investigated. This will improve our understanding of these end-caps and allow us to create a library of end-caps covering a broad range of degradation temperatures which can then be used for a variety of applications. This presentation will discuss the design, synthesis, and applications of these new thermally-sensitive molecules.
Location
University of Windsor
Grand Challenges
Viable, Healthy and Safe Communities
Preparation of a New Library of Thermally Sensitive End-Caps for Self-Immolative Polymers as a Potential Drug-Delivery Method
University of Windsor
Triggerable end-caps are a fascinating new tool in the field of material, environment and medicinal sciences that can be used for a variety of applications including the on-command degradation of self-immolative polymers. These end caps can be made sensitive to a diverse range of parameters including light, pH and enzymes. However, using heat might be of great utility for biomedical applications as it can be localized to a specific site through a number of non-invasive methods. The Trant group has prepared a number of heat-sensitive end-caps, and this study extends the scope and temperature range available to us by modifying the basic structure. These are synthesized through an efficient Diels-Alder reaction between a substituted furan and maleimide that allows for reversibility at a range of temperatures: the temperature at which the end-caps undergo retro-Diels-Alder reactions can be controlled through functionalization of these components. The role of furan functionalization with various electron donating and withdrawing groups was investigated, however steric effects played a significant role in the formation of the end-caps and it was difficult to determine the electronic effect on end-cap stability. To overcome this, furans with various para-substituted phenyls covering a range of electron withdrawing and donating groups were utilized where the steric effects are minimized, allowing the electronic effects to be investigated. This will improve our understanding of these end-caps and allow us to create a library of end-caps covering a broad range of degradation temperatures which can then be used for a variety of applications. This presentation will discuss the design, synthesis, and applications of these new thermally-sensitive molecules.