Subject Area
Chemistry
Abstract
Degradable Polymers and Networks Based on Furan-Maleimide Diels-Alder Reactions of Silyl Ether Derivatives and Maleimides. I.
I. Part 1. Two groups of silyl ether monomers, A and B, were synthesized, each containing four different monomers. The monomers of group A were obtained by reacting furfuryl alcohol with four dichlorosilanes with varying siloxane spacers. The monomers of group B were obtained by reacting n-(2-hydroxyethyl)maleimide (HEMI-1c) with the same four dichlorosilanes. Each monomer from group A was individually reacted with each monomer from group B via a Diels-Alder reaction to produce a series of sixteen degradable linear polymers with a variety of physical and chemical properties
I. Part 2. Four different networks were synthesized via a reaction between tris[(furan‐3‐yl)methoxy](methyl)silane (TSF), which was synthesized via silylation of furfuryl alcohol using trichloromethylsilane to produce trifuryl(methoxy)methylsilane (TSF). The monomers of group B were obtained by reacting n-(2-hydroxyethyl)maleimide (HEMI-1c) with four dichlorosilanes with varying siloxane spacers. Each monomer from group B was individually reacted with tris[(furan‐3‐yl)methoxy](methyl)silane (TSF) in a 3:2 molar ratio respectively, via a Diels-Alder reaction to produce four degradable networks with a variety of physical and chemical properties. Networks were obtained by heating the mixture on a hot plate at 80 °C until homogeneous and then curing it in an oven at 80 °C for 2 h. All four networks, N(TSF-1) to N(TSF-4), were synthesized following the same procedure.
I. Part 3. Seven b-type and six c-type maleimides derivatives were obtained with a significant yield enhancement. After generalizing the procedure to synthesize the maleimide derivatives, the next step will be to scale up all reactions to reach up to 50 grams in each batch for each derivative. Furthermore, all these derivatives have the potential to be converted to silyl ethers to produce new degradable linear polymers and networks.
The Michael Addition of Amines to 1,3,5-Triacryloylhexahydro-1,3,5-Triazine (TAT) as a Synthetic Route to Novel Chelating Agents. II
In this project, we successfully synthesized nine TAT-triamine derivatives through direct reactions between 1,3,5-triacryloylhexahydrotriazine (TAT) and various secondary amines. The reactions were carried out using methanol as the solvent, with a consistent 1:3 molar ratio of TAT to each amine. Despite the limited solubility of TAT in methanol, the reactions proceeded rapidly, typically completing within 10 minutes. The high product yields, ranging from 92% to 100%, were achieved through simple rotary evaporation of the solvent without the need for further purification.
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Degree Date
8-6-2024
Document Type
Dissertation
Degree Name
Ph.D.
Department
Chemistry
Advisor
David Y Son
Number of Pages
240
Format
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial 4.0 License
Recommended Citation
Alkhazalah, Reyad, "I. Degradable Polymers and Networks Based on Furan-Maleimide Diels-Alder Reactions of Silyl Ether Derivatives and Maleimides, and II. The Michael Addition of Amines to 1,3,5-Triacryloylhexahydro-1,3,5-Triazine (TAT) as a Synthetic Route to Novel Chelating Agents" (2024). Chemistry Theses and Dissertations. 48.
https://scholar.smu.edu/hum_sci_chemistry_etds/48
