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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.

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Abstract

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:
Supervisor nameSupervisor E mail
Golkaram, M.M.Golkaram@rug.nl
Degree programme: Chemistry
Thesis type: Bachelor's Thesis
Language: English
Date Deposited: 29 Jun 2018
Last Modified: 13 Jul 2018 10:00
URI: http://fse.studenttheses.ub.rug.nl/id/eprint/17519

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