Title

Thermal end-caps for use in self-immolative polymers

Submitter Information

Sarah NasriFollow

Prize Winner

Sustainable Industry

Type of Proposal

Oral Presentation

Start Date

23-3-2018 9:00 AM

End Date

23-3-2018 10:20 AM

Location

Alumni Auditorium B

Faculty

Faculty of Science

Abstract/Description of Original Work

Self-immolative polymers (SIPs) are materials that spontaneously depolymerize, monomer unit by monomer unit, at room temperature once activated. This is a new class of polymers first reported a decade ago. These molecules can be stabilized indefinitely simply by attaching an “end-cap” to one end of the polymer after they are made. When this end-cap is removed, the polymer can begin breaking down itself in the matter of hours or days. In traditional biodegradable polymers, degradation does not occur so easily, as often requiring an enzyme to cleave every single bond between the monomers units. This causes a longer degradation over between months to years. Application of self-immolative polymers will essentially be dictated by the end-caps responsible in keeping them together. The wide possibilities of end-cap will offer different stimuli that is required to remove it, be it light, heat, reduction, oxidation and pH. The retro Diels-Alder has one of the most heavily studied reactions. The reversibility of the reaction of the furan and maleimide makes these types of compound perfect to become end-caps. Over the course of 2017, the Trant Team experimented with different combinations of various electron withdrawing and electron donating groups within a Diels-Alder molecule to see how it can be manipulated to obtain different degradation temperatures. The end-result was a small library of compounds responsive to temperatures between 35 ºC to 110 ºC. These interesting molecules could be useful for a wide variety of applications in materials, environmental, and biomedical science. This presentation will report on our studies into these compounds, provide an introduction to self-immolative polymers, and show the potential of these systems for biomedical engineering.

Share

COinS
 
Mar 23rd, 9:00 AM Mar 23rd, 10:20 AM

Thermal end-caps for use in self-immolative polymers

Alumni Auditorium B

Self-immolative polymers (SIPs) are materials that spontaneously depolymerize, monomer unit by monomer unit, at room temperature once activated. This is a new class of polymers first reported a decade ago. These molecules can be stabilized indefinitely simply by attaching an “end-cap” to one end of the polymer after they are made. When this end-cap is removed, the polymer can begin breaking down itself in the matter of hours or days. In traditional biodegradable polymers, degradation does not occur so easily, as often requiring an enzyme to cleave every single bond between the monomers units. This causes a longer degradation over between months to years. Application of self-immolative polymers will essentially be dictated by the end-caps responsible in keeping them together. The wide possibilities of end-cap will offer different stimuli that is required to remove it, be it light, heat, reduction, oxidation and pH. The retro Diels-Alder has one of the most heavily studied reactions. The reversibility of the reaction of the furan and maleimide makes these types of compound perfect to become end-caps. Over the course of 2017, the Trant Team experimented with different combinations of various electron withdrawing and electron donating groups within a Diels-Alder molecule to see how it can be manipulated to obtain different degradation temperatures. The end-result was a small library of compounds responsive to temperatures between 35 ºC to 110 ºC. These interesting molecules could be useful for a wide variety of applications in materials, environmental, and biomedical science. This presentation will report on our studies into these compounds, provide an introduction to self-immolative polymers, and show the potential of these systems for biomedical engineering.