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Synthesis and Characterization of Novel Supramolecular Polymers

Mulder, Pascal (2018) Synthesis and Characterization of Novel Supramolecular Polymers. Bachelor's Thesis, Chemistry.

Final version, P. Mulder, Synthesis and characterization of novel supramolecular polymers.pdf

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The goal of this thesis was to synthesize and characterize supramolecular polymers with unique structures; namely, star or brush shaped architectures. First a supramolecular star core was tried to synthesize. The hydrogen bonding thymine stickers were attached to the core with a copper-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction. From 1H NMR analysis a conversion of 53 % could be determined. This means that each star core has only one or two thymine end-groups instead of three. Since, the product could not be isolated with column chromatography, it could not be used to form a supramolecular star network. Next, a brush shaped supramolecular polymer was synthesized starting from the synthesis of a 2,7-diamide-1,8- naphthyridine (Napy) based sticker. During the synthesis all steps except the final step resulted in a quantitative yield. In the final step, the double bond of the monomer was introduced by reacting 1-(6-isocyanatohexyl)-3-(7-oxo-7,8-dihydro-1,8-naphthyridin-2-yl)urea with 2-hydroxyl acrylate. This reaction was catalysed by dibutyltin dilaurate (DBDTL) and the product was obtained in a 66 % yield. The Napy monomer was polymerized using a reversible addition-fragmentation chain-transfer (RAFT) polymerization. Using 2-(Dodecylthiocarbonothioylthio)-2-methylpropionic acid (DDMAT) as chain transfer agent (CTA), a polymer with (M_n ) ̅ = 4,050 was obtained. The thermal properties were determined with thermographic analysis (TGA) and differential scanning calorimetry (DSC). From the measurements it could be concluded that a high glass transition temperature (Tg) polymer was obtained with a decomposition temperature of 238.4 °C. Also, a copolymer with different compositions was synthesized from the Napy-based monomer and n-butyl acrylate by a RAFT polymerization using S,S-Dibenzyl trithiocarbonate (DBTTC) as CTA. The thermal properties were compared with pure poly (n-butyl acrylate). DSC confirmed that the Tg of the copolymers increased with increasing amounts of Napy side groups, which is a result of the increasing hydrogen bonding interactions. Eventually, the Napy-based polymers can be used as backbone to create a well-defined supramolecular brush network with ureidopyrimidinone (UPy) based side chains, introducing new properties to the field of supramolecular polymer chemistry.

Item Type: Thesis (Bachelor's Thesis)
Supervisor name: Golkaram, M.
Degree programme: Chemistry
Thesis type: Bachelor's Thesis
Language: English
Date Deposited: 29 Jun 2018
Last Modified: 13 Jul 2018 10:00

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