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Title:Funkcionalizacija hidrokinonskih obročev z okso-nukleofilnimi substitucijami za pripravo konjugiranih polielektrolitov
Authors:ID Šilak, Matej (Author)
ID Kovačič, Sebastijan (Mentor) More about this mentor... New window
Files:.pdf UN_Silak_Matej_2024.pdf (1,97 MB)
MD5: CA220175043F106F7337ADB1F3991FD7
 
Language:Slovenian
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Engineering
Abstract:Diplomska naloga je kombinacija organske sinteze, polimerne kemije in organske analize. Izvedli smo sintezo malih molekul, ki služijo kot prekurzorji za pripravo konjugiranih polielektrolitnih (CPE) polimerov. Prekurzorje, 3,3'-((2,5-dibromo-1,4-fenilen)bis(okso))bis(N,N,N-trimetilpropan-1-aminijev) bromid, 3,3'-((2,5-dietinill-1,4-fenilen)bis(oksi))bis(N,N,N-trimetilpropan-1-aminijev) bromid in 3,3'-((2,5-diformil-1,4-fenilen)bis(okso))bis(N,N,N-trimetilpropan-1-aminijev) bromid smo pripravili z okso-nukleofilno substitucijo, natančneje, izvedli smo t. i. Williamsovo eintezo etra. Prekurzor 1,3,5-tris(4-bromofenil)benzen, smo sintetizirali s kislinsko katalizirano aldolno kondenzacijo, pri kateri nastane trimerna spojina. Tako pripravljene prekurzorje, smo v nadaljevanju uporabili za pripravo CPE z reakcijami Sonogashira-Hagihara in Suzuki-Miyaura navzkrižnim pripajanjem ter s Schiff-bazno reakcijo. Monomere in polimere smo analizirali z uporabo 1H NMR spektroskopije (prekurzorji), FTIR spektroskopije (polimeri), DRS UV-Vis spektroskopije (polimeri) in CHN elementne analize (prekurzorji in polimeri). Uspešno smo izvedli sintezo treh prekurzorjev in dveh CPE polimerov. Strukturo prekurzorjev smo potrdili z 1H NMR. Strukturo polimerov smo potrdili z FTIR spektroskopijo. Z DRS UV-Vis smo polimeroma določili optične lastnosti. Rezultati elementne analize dopolnjujejo NMR in FTIR rezultate in potrjujejo željene molekule in makromolekule.
Keywords:Williamsova sinteza etra, Sonogashira-Hagihara reakcija, Suzuki-Miyaura reakcija, Schiff-bazna reakcija, konjugirani polielektrolitni polimeri
Place of publishing:Maribor
Year of publishing:2024
PID:20.500.12556/DKUM-90730 New window
Publication date in DKUM:15.10.2024
Views:0
Downloads:11
Metadata:XML DC-XML DC-RDF
Categories:KTFMB - FKKT
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Licences

License:CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
Link:http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.
Licensing start date:18.09.2024

Secondary language

Language:English
Title:Functionalization of hydroquinone rings by oxo-nucleophilic substitutions for the preparation of conjugated polyelectrolytes
Abstract:The diploma thesis is a combination of organic synthesis, polymer chemistry and organic analysis. We have carried out the synthesis of small molecules that serve as precursors for the preparation of conjugated polyelectrolyte (CPE) polymers. The precursors, 3,3'-((2,5-dibromo-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropane-1-aminium)bromide, 3,3'-((2,5-diethynyl-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropane-1-aminium)bromide, and 3,3'-((2,5-diformyl-1,4-phenylene)bis(oxy))bis(N,N,N-trimethylpropan-1-aminium)bromide were prepared by oxo-nucleophilic substitution, namely by carrying out the so-called Williamson ether synthesis. The precursor, 1,3,5-tris(4-bromophenyl)benzene, was synthesized by acid-catalyzed aldol condensation, resulting in a trimeric compound. These precursors were subsequently used to prepare CPEs by Sonogashira-Hagihara and Suzuki-Miyaura cross-coupling reactions and by a Schiff base reaction. The monomers and polymers were analyzed by ¹H-NMR spectroscopy (precursors), FTIR spectroscopy (polymers), DRS-UV-Vis spectroscopy (polymers) and CHN elemental analysis (precursors and polymers). Finally, we successfully synthesized three precursors and two CPE polymers. The structure of the precursors was confirmed by ¹H NMR. The structure of the polymers was confirmed by FTIR spectroscopy. The optical properties of the polymers were determined by DRS-UV-Vis spectroscopy. The results of the elemental analysis complement the NMR and FTIR spectroscopy analysis and confirm the desired molecules and macromolecules.
Keywords:Williamson ether synthesis, Sonogashira-Hagihara reaction, Suzuki-Miyaura reaction, Schiff base reaction, conjugated polyelectrolyte polymers (CPE)


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